Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions

  • Raquel P. Herrera
Part of the following topical collections:
  1. Hydrogen Transfer Reactions


The reduction of different carbon–carbon or carbon–heteroatom double bonds is a powerful tool that generates in many cases new stereogenic centers. In the last decade, the organocatalytic version of these transformations has attracted more attention, and remarkable progress has been made in this way. Organocatalysts such as chiral Brønsted acids, thioureas, chiral secondary amines or Lewis bases have been successfully used for this purpose. In this context, this chapter will cover pioneering and seminal examples using Hantzsch dihydropyridines 1 and trichlorosilane 2 as reducing agents. More recent examples will be also cited in order to cover as much as possible the complete research in this field.


Transfer hydrogenation Organocatalysis Hantzsch ester Trichlorosilane Phosphoric acid Aminocatalysis Thioureas Lewis bases Reduction Hydrosilylation 


  1. 1.
    Nugent TC (ed) (2010) Chiral amine synthesis. Wiley-VCH, WeinheimGoogle Scholar
  2. 2.
    Kobayashi S, Ishitani H (1999) Chem Rev 99:1069–1094CrossRefGoogle Scholar
  3. 3.
    Palmer MJ, Wills M (1999) Tetrahedron Asymmetry 10:2045–2061CrossRefGoogle Scholar
  4. 4.
    Carpentier J-F, Bette V (2002) Curr Org Chem 6:913–936CrossRefGoogle Scholar
  5. 5.
    Tang W, Zhang X (2003) Chem Rev 103:3029–3069CrossRefGoogle Scholar
  6. 6.
    Blaser H-U, Malan C, Pugin B, Spindler F, Steiner H, Studer M (2003) Adv Synth Catal 345:103–151CrossRefGoogle Scholar
  7. 7.
    Riant O, Mostefaï N, Courmarcel J (2004) Synthesis 2943–2958Google Scholar
  8. 8.
    Tararov VI, Börner A (2005) Synlett 203–211Google Scholar
  9. 9.
    Samec JSM, Bäckvall J-E, Andersson PG, Brandt P (2006) Chem Soc Rev 35:237–248CrossRefGoogle Scholar
  10. 10.
    Cho BT (2006) Tetrahedron 62:7621–7643CrossRefGoogle Scholar
  11. 11.
    Berkessel A, Gröger H (2005) Asymmetric organocatalysis. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  12. 12.
    Dalko PI (ed) (2007) Enantioselective organocatalysis. Wiley, New YorkGoogle Scholar
  13. 13.
    Dalko PI (ed) (2013) Comprehensive enantioselective organocatalysis. Wiley-VCH, WeinheimGoogle Scholar
  14. 14.
    Adolfsson H (2005) Angew Chem Int Ed 44:3340–3342CrossRefGoogle Scholar
  15. 15.
    Tripathi RP, Verma SS, Pandey J, Tiwari VK (2008) Curr Org Chem 12:1093–1115CrossRefGoogle Scholar
  16. 16.
    Rueping M, Dufour J, Schoepke FR (2011) Green Chem 13:1084–1105CrossRefGoogle Scholar
  17. 17.
    Zheng C, You S-L (2012) Chem Soc Rev 41:2498–2518CrossRefGoogle Scholar
  18. 18.
    Benaglia M, Bonsignore M, Genoni A (2013) In: Rios R (ed) Stereoselective organocatalysis: bond formation methodologies and activation modes. Wiley, Hoboken, pp 529–558CrossRefGoogle Scholar
  19. 19.
    Li G, Antilla JC (2013) In: Dalko PI (ed) Comprehensive enantioselective organocatalysis. Wiley-VCH, Weinheim, pp 941–974CrossRefGoogle Scholar
  20. 20.
    Kortmann F, Minnaard A (2013) In: Andrushko V, Andrushko N (eds) Stereoselective synthesis of drugs and natural products. Wiley, Hoboken, pp 993–1014Google Scholar
  21. 21.
    Ouellet SG, Walji AM, MacMillan DWC (2007) Acc Chem Res 40:1327–1339CrossRefGoogle Scholar
  22. 22.
    You S-L (2007) Chem Asian J 2:820–827CrossRefGoogle Scholar
  23. 23.
    Connon SJ (2007) Org Biomol Chem 5:3407–3417CrossRefGoogle Scholar
  24. 24.
    Wang C, Wu X, Xiao J (2008) Chem Asian J 3:1750–1770CrossRefGoogle Scholar
  25. 25.
    Rueping M, Sugiono E, Schoepke FR (2010) Synlett 852–865Google Scholar
  26. 26.
    Bernardi L, Fochi M, Franchini MC, Ricci A (2012) Org Biomol Chem 10:2911–2922CrossRefGoogle Scholar
  27. 27.
    Kočovský P, Malkov AV (2007) In: Dalko PI (ed) Enantioselective organocatalysis. Reactions and experimental procedures. Wiley-VCH, Weinheim, pp 275–278Google Scholar
  28. 28.
    Kočovský P, Stončius S (2010) In: Nugent TC (ed) Chiral amine synthesis. Wiley-VCH, Weinheim, pp 131–156CrossRefGoogle Scholar
  29. 29.
    Guizzetti S, Benaglia M (2010) Eur J Org Chem, 5529–5554Google Scholar
  30. 30.
    Jones S, Warner CJA (2012) Org Biomol Chem 10:2189–2200CrossRefGoogle Scholar
  31. 31.
    Zhu C, Akiyama T (2009) Org Lett 11:4180–4183CrossRefGoogle Scholar
  32. 32.
    Sakamoto T, Mori K, Akiyama T (2012) Org Lett 14:3312–3315CrossRefGoogle Scholar
  33. 33.
    Zhu C, Saito K, Yamanaka M, Akiyama T (2015) Acc Chem Res 48:388–398CrossRefGoogle Scholar
  34. 34.
    Rossi S, Benaglia M, Massolo E, Raimondi L (2014) Catal Sci Technol 4:2708–2723CrossRefGoogle Scholar
  35. 35.
    Hantzsch A (1881) Ber. 14:1637–1638CrossRefGoogle Scholar
  36. 36.
    Hantzsch A (1882) Justus Liebigs Ann Chem 215:1–82CrossRefGoogle Scholar
  37. 37.
    Singh S, Batra UK (1989) Ind J Chem Sect B 28:1–2Google Scholar
  38. 38.
    Steevens JB, Pandit UK (1983) Tetrahedron 39:1395–1400CrossRefGoogle Scholar
  39. 39.
    Fujii M, Aida T, Yoshihara M, Ohno A (1989) Bull Chem Soc Jpn 62:3845–3847CrossRefGoogle Scholar
  40. 40.
    Itoh T, Nagata K, Kurihara A, Miyazaki M, Ohsawa A (2002) Tetrahedron Lett 43:3105–3108CrossRefGoogle Scholar
  41. 41.
    Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M (2005) Org Lett 7:3781–3783CrossRefGoogle Scholar
  42. 42.
    Hoffmann S, Seayad AM, List B (2005) Angew Chem Int Ed 44:7424–7427CrossRefGoogle Scholar
  43. 43.
    Itoh T, Nagata K, Miyazaki M, Ishikawa H, Kurihara A, Ohsawa A (2004) Tetrahedron 60:6649–6655CrossRefGoogle Scholar
  44. 44.
    Rueping M, Azap C, Sugiono E, Theissmann T (2005) Synlett, 2367–2369Google Scholar
  45. 45.
    Akiyama T (2007) Chem Rev 107:5744–5758CrossRefGoogle Scholar
  46. 46.
    Terada M (2008) Chem Commun, 4097–4112Google Scholar
  47. 47.
    Adair G, Mukherjee S, List B (2008) Aldrichim Acta 41:31–39Google Scholar
  48. 48.
    You S-L, Cai Q, Zeng M (2009) Chem Soc Rev 38:2190–2201CrossRefGoogle Scholar
  49. 49.
    Kampen D, Reisinger CM, List B (2010) Top Curr Chem 291:395–456CrossRefGoogle Scholar
  50. 50.
    Terada M (2010) Synthesis, 1929–1982Google Scholar
  51. 51.
    Terada M (2010) Bull Chem Soc Jpn 83:101–119CrossRefGoogle Scholar
  52. 52.
    Yu J, Shi F, Gong L-Z (2011) Acc Chem Res 44:1156–1171CrossRefGoogle Scholar
  53. 53.
    Terada M (2011) Curr Org Chem 15:2227–2256CrossRefGoogle Scholar
  54. 54.
    Rueping M, Kuenkel A, Atodiresei I (2011) Chem Soc Rev 40:4539–4549CrossRefGoogle Scholar
  55. 55.
    Schenker S, Zamfir A, Freund M, Tsogoeva SB (2011) Eur J Org Chem 2209–2222Google Scholar
  56. 56.
    Čorić I, Vellalath S, Müller S, Cheng X, List B (2013) Top Organomet Chem 44:165–194CrossRefGoogle Scholar
  57. 57.
    Parmar D, Sugiono E, Raja S, Rueping M (2014) Chem Rev 114:9047–9153CrossRefGoogle Scholar
  58. 58.
    Held FE, Grau D, Tsogoeva SB (2015) Molecules 20:16103–16126CrossRefGoogle Scholar
  59. 59.
    Marcelli T, Hammar P, Himo F (2008) Chem Eur J 14:8562–8571CrossRefGoogle Scholar
  60. 60.
    Simón L, Goodman JM (2008) J Am Chem Soc 130:8741–8747CrossRefGoogle Scholar
  61. 61.
    Marcelli T, Hammar P, Himo F (2009) Adv Synth Catal 351:525–529CrossRefGoogle Scholar
  62. 62.
    Storer RI, Carrera DE, Ni Y, MacMillan DWC (2006) J Am Chem Soc 128:84–86CrossRefGoogle Scholar
  63. 63.
    Kang Q, Zhao Z-A, You S-L (2007) Adv Synth Catal 349:1657–1660CrossRefGoogle Scholar
  64. 64.
    Kang Q, Zhao Z-A, You S-L (2008) Org Lett 10:2031–2034CrossRefGoogle Scholar
  65. 65.
    Li G, Liang Y, Antilla JC (2007) J Am Chem Soc 129:5830–5831CrossRefGoogle Scholar
  66. 66.
    Rueping M, Antonchick AP, Theissmann T (2006) Angew Chem Int Ed 45:3683–3686CrossRefGoogle Scholar
  67. 67.
    Katritzky AR, Rachwal S, Rachwal B (1996) Tetrahedron 52:15031–15070CrossRefGoogle Scholar
  68. 68.
    Rakotoson JH, Fabre N, Jacquemond-Collet I, Hannedouche S, Fouraste I, Moulis C (1998) Planta Med 64:762–763CrossRefGoogle Scholar
  69. 69.
    Jacquemond-Collet I, Hannedouche S, Fabre N, Fouraste I, Moulis C (1999) Phytochem 51:1167–1169CrossRefGoogle Scholar
  70. 70.
    Houghton PJ, Woldemariam TZ, Watanabe Y, Yates M (1999) Planta Med 65:250–254CrossRefGoogle Scholar
  71. 71.
    Rueping M, Theissmann T, Antonchick AP (2006) Synlett, 1071–1074Google Scholar
  72. 72.
    Rueping M, Theissmann T, Raja S, Bats JW (2008) Adv Synth Catal 350:1001–1006CrossRefGoogle Scholar
  73. 73.
    Guo Q-S, Du D-M, Xu J (2008) Angew Chem Int Ed 47:759–762CrossRefGoogle Scholar
  74. 74.
    Metallinos C, Barrett FB, Xu S (2008) Synlett, 720–724Google Scholar
  75. 75.
    Han Z-Y, Xiao H, Chen X-H, Gong L-Z (2009) J Am Chem Soc 131:9182–9183CrossRefGoogle Scholar
  76. 76.
    Rueping M, Sugiono E, Steck A, Theissmann T (2010) Adv Synth Catal 352:281–287CrossRefGoogle Scholar
  77. 77.
    Rueping M, Theissmann T (2010) Chem Sci 1:473–476CrossRefGoogle Scholar
  78. 78.
    Rueping M, Theissmann T, Stoeckel M, Antonchick AP (2011) Org Biomol Chem 9:6844–6850CrossRefGoogle Scholar
  79. 79.
    Li G, Liu H, Lv G, Wang Y, Fu Q, Tang Z (2015) Org Lett 17:4125–4127CrossRefGoogle Scholar
  80. 80.
    Tu X-F, Gong L-Z (2012) Angew Chem Int Ed 51:11346–11349CrossRefGoogle Scholar
  81. 81.
    Shi F, Gong L-Z (2012) Angew Chem Int Ed 51:11423–11425CrossRefGoogle Scholar
  82. 82.
    Chen M-W, Cai X-F, Chen Z-P, Shi L, Zhou Y-G (2014) Chem Commun 50:12526–12529CrossRefGoogle Scholar
  83. 83.
    Guo R-N, Chen Z-P, Cai X-F, Zhou Y-G (2014) Synthesis 46:2751–2756CrossRefGoogle Scholar
  84. 84.
    Aillerie A, de Talancé VL, Moncomble A, Bousquet T, Pélinski L (2014) Org Lett 16:2982–2985CrossRefGoogle Scholar
  85. 85.
    Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano K-I, Furukawa M (1986) Antimicrob Agents Chemother 29:163–164CrossRefGoogle Scholar
  86. 86.
    Seiyaku D (1992) Drugs Future 17:559–563CrossRefGoogle Scholar
  87. 87.
    Rueping M, Stoeckel M, Sugiono E, Theissmann T (2010) Tetrahedron 66:6565–6568CrossRefGoogle Scholar
  88. 88.
    Friedländer P (1882) Ber Dtsch Chem Ges 15:2572–2575CrossRefGoogle Scholar
  89. 89.
    Marco-Contelles J, Pérez-Mayoral E, Samadi A, Carreiras MC, Soriano E (2009) Chem Rev 109:2652–2671CrossRefGoogle Scholar
  90. 90.
    Ren L, Lei T, Ye J-X, Gong L-Z (2012) Angew Chem Int Ed 51:771–774CrossRefGoogle Scholar
  91. 91.
    Rueping M, Antonchick AP (2007) Angew Chem Int Ed 46:4562–4565CrossRefGoogle Scholar
  92. 92.
    Bohlmann F, Rahtz D (1957) Chem Ber 90:2265–2272CrossRefGoogle Scholar
  93. 93.
    Bagley MC, Brace C, Dale JW, Ohnesorge M, Phillips NG, Xiong X, Bower J (2002) J Chem Soc Perkin Trans 1:1663–1671CrossRefGoogle Scholar
  94. 94.
    Sklenicka HM, Hsung RP, McLaughlin MJ, Wie L-L, Gerasyuto AI, Brennessel WB (2002) J Am Chem Soc 124:10435–10442CrossRefGoogle Scholar
  95. 95.
    Rueping M, Antonchick AP, Theissmann T (2006) Angew Chem Int Ed 45:6751–6755CrossRefGoogle Scholar
  96. 96.
    Tietze LF, Brasche G, Gericke KM (eds) (2006) Domino reactions in organic synthesis. Wiley-VCH, WeinheimGoogle Scholar
  97. 97.
    Enders D, Grondal C, Hüttl MRM (2007) Angew Chem Int Ed 46:1570–1581CrossRefGoogle Scholar
  98. 98.
    Walji AM, MacMillan DWC (2007) Synlett, 1477–1489Google Scholar
  99. 99.
    Rueping M, Antonchick AP (2008) Angew Chem Int Ed 45:5836–5838CrossRefGoogle Scholar
  100. 100.
    Rueping M, Tato F, Schoepke FR (2010) Chem Eur J 16:2688–2691CrossRefGoogle Scholar
  101. 101.
    Fantin M, Marti M, Auberson YP, Morari M (2007) J Neurochem 103:2200–2211CrossRefGoogle Scholar
  102. 102.
    TenBrink RE, Im WB, Sethy VH, Tang AH, Carter DB (1994) J Med Chem 37:758–768CrossRefGoogle Scholar
  103. 103.
    Li S, Tian X, Hartley DM, Feig LA (2006) J Neurosci 26:1721–1729CrossRefGoogle Scholar
  104. 104.
    Patel M, McHush RJ Jr, Cordova BC, Klabe RM, Erickson-Viitanen S, Trainor GL, Rodgers JD (2000) Bioorg Med Chem Lett 10:1729–1731CrossRefGoogle Scholar
  105. 105.
    Shi F, Tan W, Zhang H-H, Li M, Ye Q, Ma G-H, Tu S-J, Li G (2013) Adv Synth Catal 355:3715–3726CrossRefGoogle Scholar
  106. 106.
    Liao H-H, Hsiao C-C, Sugiono E, Rueping M (2013) Chem Commun 49:7953–7955CrossRefGoogle Scholar
  107. 107.
    Sugiono E, Rueping M (2013) Beilstein J Org Chem 9:2457–2462CrossRefGoogle Scholar
  108. 108.
    Hsiao C-C, Liao H-H, Sugiono E, Atodiresei I, Rueping M (2013) Chem Eur J 19:9775–9779CrossRefGoogle Scholar
  109. 109.
    Wang Z, Ai F, Wang Z, Zhao W, Zhu G, Lin Z, Sun J (2015) J Am Chem Soc 137:383–389CrossRefGoogle Scholar
  110. 110.
    Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138–5175CrossRefGoogle Scholar
  111. 111.
    Seayed J, List B (2005) Org Biomol Chem 3:719–724CrossRefGoogle Scholar
  112. 112.
    List B (2006) Chem Commun, 819–824Google Scholar
  113. 113.
    Marigo M, Jørgensen KA (2006) Chem Commun, 2001–2011Google Scholar
  114. 114.
    Guillena G, Ramón DJ (2006) Tetrahedron Asymmetry 17:1465–1492CrossRefGoogle Scholar
  115. 115.
    Sulzer-Mossé S, Alexakis A (2007) Chem Commun, 3123–3135Google Scholar
  116. 116.
    Tsogoeva SB (2007) Eur J Org Chem, 1701–1716Google Scholar
  117. 117.
    Vicario JL, Badía D, Carrillo L (2007) Synthesis, 2065–2092Google Scholar
  118. 118.
    Almaşi D, Alonso DA, Najera C (2007) Tetrahedron Asymmetry 18:299–365CrossRefGoogle Scholar
  119. 119.
    Pellissier H (2007) Tetrahedron 63:9267–9331CrossRefGoogle Scholar
  120. 120.
    Dondoni A, Massi A (2008) Angew Chem Int Ed 47:4638–4660CrossRefGoogle Scholar
  121. 121.
    Melchiorre P, Marigo M, Carlone A, Bartoli G (2008) Angew Chem Int Ed 47:6138–6171CrossRefGoogle Scholar
  122. 122.
    Gruttadauria M, Giacalone F, Noto R (2009) Adv Synth Catal 351:33–57CrossRefGoogle Scholar
  123. 123.
    Bertelsen S, Jørgensen KA (2009) Chem Soc Rev 38:2178–2189CrossRefGoogle Scholar
  124. 124.
    Ueda M, Kano T, Maruoka K (2009) Org Biomol Chem 7:2005–2012CrossRefGoogle Scholar
  125. 125.
    Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA (2010) Angew Chem Int Ed 49:2668–2679CrossRefGoogle Scholar
  126. 126.
    Nielsen M, Worgull D, Zweifel T, Gschwend B, Bertelsen S, Jørgensen KA (2011) Chem Commun 47:632–649CrossRefGoogle Scholar
  127. 127.
    Marqués-López E, Herrera RP (2011) Curr Org Chem 15:2311–2327CrossRefGoogle Scholar
  128. 128.
    Jurberg ID, Chatterjee I, Tannert R, Melchiorre P (2013) Chem Commun 49:4869–4883CrossRefGoogle Scholar
  129. 129.
    Paz BM, Jiang H, Jørgensen KA (2015) Chem Eur J 21:1846–1853CrossRefGoogle Scholar
  130. 130.
    Yang JW, Fonseca MTH, List B (2004) Angew Chem Int Ed 43:6660–6662CrossRefGoogle Scholar
  131. 131.
    Yang JW, Fonseca MTH, Vignola N, List B (2005) Angew Chem Int Ed 44:108–110CrossRefGoogle Scholar
  132. 132.
    Ouellet SG, Tuttle JB, MacMillan DWC (2005) J Am Chem Soc 127:32–33CrossRefGoogle Scholar
  133. 133.
    Tuttle JB, Ouellet SG, MacMillan DWC (2006) J Am Chem Soc 128:12662–12663CrossRefGoogle Scholar
  134. 134.
    Huang Y, Walji AM, Larsen CH, MacMillan DWC (2005) J Am Chem Soc 127:15051–15053CrossRefGoogle Scholar
  135. 135.
    Mayer S, List B (2006) Angew Chem Int Ed 45:4193–4195CrossRefGoogle Scholar
  136. 136.
    Martin NJA, List B (2006) J Am Chem Soc 128:13368–13369CrossRefGoogle Scholar
  137. 137.
    Eey ST-C, Lear MJ (2010) Org Lett 12:5510–5513CrossRefGoogle Scholar
  138. 138.
    Akagawa K, Akabane H, Sakamoto S, Kudo K (2008) Org Lett 10:2035–2037CrossRefGoogle Scholar
  139. 139.
    Akagawa K, Akabane H, Sakamoto S, Kudo K (2009) Tetrahedron Asymmetry 20:461–466CrossRefGoogle Scholar
  140. 140.
    Hoffman TJ, Dash J, Rigby JH, Arseniyadis S, Cossy J (2009) Org Lett 11:2756–2759CrossRefGoogle Scholar
  141. 141.
    Schreiner PR (2003) Chem Soc Rev 32:289–296CrossRefGoogle Scholar
  142. 142.
    Takemoto Y (2005) Org Biomol Chem 3:4299–4306CrossRefGoogle Scholar
  143. 143.
    Breuzard JAJ, Christ-Tommasino ML, Lemaire M (2005) Top Organomet Chem 15:231–270CrossRefGoogle Scholar
  144. 144.
    Connon SJ (2006) Chem Eur J 12:5418–5427CrossRefGoogle Scholar
  145. 145.
    Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520–1543CrossRefGoogle Scholar
  146. 146.
    Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713–5743CrossRefGoogle Scholar
  147. 147.
    Zhang Z, Schreiner PR (2009) Chem Soc Rev 38:1187–1198CrossRefGoogle Scholar
  148. 148.
    Marqués-López E, Herrera RP (2009) An Quim 105:5–12Google Scholar
  149. 149.
    Kotke M, Schreiner PR (2009) In: Pihko PM (ed) Hydrogen bonding in organic synthesis. Wiley-VCH, Weinheim, pp 141–351CrossRefGoogle Scholar
  150. 150.
    Connon SJ (2009) Synlett, 354–376Google Scholar
  151. 151.
    Marqués-López E, Herrera RP (2012) In: Pignataro B (ed) New strategies in chemical synthesis and catalysis. Wiley-VCH, Weinheim, pp 175–199CrossRefGoogle Scholar
  152. 152.
    Narayanaperumal S, Rivera DG, Silva RC, Paixão MW (2013) ChemCatChem 5:2756–2773CrossRefGoogle Scholar
  153. 153.
    Jakab G, Schreiner PR (2013) In: Dalko P (ed) Comprehensive enantioselective organocatalysis. Wiley-VCH, Weinheim, pp 315–341CrossRefGoogle Scholar
  154. 154.
    Serdyuk OV, Heckel CM, Tsogoeva SB (2013) Org Biomol Chem 11:7051–7071CrossRefGoogle Scholar
  155. 155.
    Menche D, Arikan F (2006) Synlett, 841–844Google Scholar
  156. 156.
    Martin NJA, Ozores L, List B (2007) J Am Chem Soc 129:8976–8977CrossRefGoogle Scholar
  157. 157.
    Zhang Z, Schreiner PR (2007) Synthesis, 2559–2564Google Scholar
  158. 158.
    Martin NJA, Cheng X, List B (2008) J Am Chem Soc 130:13862–13863CrossRefGoogle Scholar
  159. 159.
    Schneider JF, Falk FC, Fröhlich R, Paradies J (2010) Eur J Org Chem, 2265–2269Google Scholar
  160. 160.
    Schneider JF, Lauber MB, Muhr V, Kratzer D, Paradies J (2011) Org Biomol Chem 9:4323–4327CrossRefGoogle Scholar
  161. 161.
    Massolo E, Benaglia M, Orlandi M, Rossi S, Celentano G (2015) Chem Eur J 21:3589–3595CrossRefGoogle Scholar
  162. 162.
    Martinelli E, Vicini AC, Mancinelli M, Mazzanti A, Zani P, Bernardi L, Fochi M (2015) Chem Commun 51:658–660CrossRefGoogle Scholar
  163. 163.
    Denmark SE, Fu J (2003) Chem Rev 103:2763–2793CrossRefGoogle Scholar
  164. 164.
    Denmark SE, Beutner GL (2008) Angew Chem Int Ed 47:1560–1638CrossRefGoogle Scholar
  165. 165.
    Iwasaki F, Onomura O, Mishima K, Kanematsu T, Maki T, Matsumura Y (2001) Tetrahedron Lett 42:2525–2527CrossRefGoogle Scholar
  166. 166.
    Baudequin C, Chaturvedi D, Tsogoeva SB (2007) Eur J Org Chem, 2623–2629Google Scholar
  167. 167.
    Xue Z-Y, Jiang Y, Yuan W-C, Zhang X-M (2010) Eur J Org Chem, 616–619Google Scholar
  168. 168.
    Zheng H, Deng J, Lin W, Zhang X (2007) Tetrahedron Lett 48:7934–7937CrossRefGoogle Scholar
  169. 169.
    Xue Z-Y, Jiang Y, Peng X-Z, Yuan W-C, Zhang X-M (2010) Adv Synth Catal 352:2132–2136CrossRefGoogle Scholar
  170. 170.
    Chen X, Zheng Y, Shu C, Yuan W, Liu B, Zhang X (2011) J Org Chem 76:9109–9115CrossRefGoogle Scholar
  171. 171.
    Genoni A, Benaglia M, Massolo E, Rossi S (2013) Chem Commun 49:8365–8367CrossRefGoogle Scholar
  172. 172.
    Barrulas PC, Genoni A, Benaglia M, Burke AJ (2014) Eur J Org Chem, 7339–7342Google Scholar
  173. 173.
    Onomura O, Kouchi Y, Iwasaki F, Matsumura Y (2006) Tetrahedron Lett 47:3751–3754CrossRefGoogle Scholar
  174. 174.
    Wang Z, Wei S, Wang C, Sun J (2007) Tetrahedron Asymmetry 18:705–709CrossRefGoogle Scholar
  175. 175.
    Kanemitsu T, Umehara A, Haneji R, Nagata K, Itoh T (2012) Tetrahedron 68:3893–3898CrossRefGoogle Scholar
  176. 176.
    Malkov AV, Mariani A, MacDougall KN, Kočovský P (2004) Org Lett 6:2253–2256CrossRefGoogle Scholar
  177. 177.
    Malkov AV, Stončius S, MacDougall KN, Mariani A, McGeoch GD, Kočovský P (2006) Tetrahedron 62:264–284CrossRefGoogle Scholar
  178. 178.
    Malkov AV, Figlus M, Stončius S, Kočovský P (2007) J Org Chem 72:1315–1325CrossRefGoogle Scholar
  179. 179.
    Malkov AV, Stončius S, Kočovský P (2007) Angew Chem Int Ed 46:3722–3724CrossRefGoogle Scholar
  180. 180.
    Malkov AV, Vranková K, Stončius S, Kočovský P (2009) J Org Chem 74:5839–5849CrossRefGoogle Scholar
  181. 181.
    Malkov AV, Vranková K, Sigerson RC, Stončius S, Kočovský P (2009) Tetrahedron 65:9481–9486CrossRefGoogle Scholar
  182. 182.
    Ge X, Qian C, Chen X (2014) Tetrahedron Asymmetry 25:1450–1455CrossRefGoogle Scholar
  183. 183.
    Wang Z, Ye X, Wei S, Wu P, Zhang A, Sun J (2006) Org Lett 8:999–1001CrossRefGoogle Scholar
  184. 184.
    Zhou L, Wang Z, Wei S, Sun J (2007) Chem Commun, 2977–2979Google Scholar
  185. 185.
    Collados JF, Quiroga-Feijóo ML, Alvarez-Ibarra C (2009) Eur J Org Chem, 3357–3367Google Scholar
  186. 186.
    Xiao Y-C, Wang C, Yao Y, Sun J, Chen Y-C (2011) Angew Chem Int Ed 50:10661–10664CrossRefGoogle Scholar
  187. 187.
    Wang ZY, Wang C, Zhou L, Sun J (2013) Org Biomol Chem 11:787–797CrossRefGoogle Scholar
  188. 188.
    Wang Z, Cheng M, Wu P, Wei S, Sun J (2006) Org Lett 8:3045–3048CrossRefGoogle Scholar
  189. 189.
    Wu P, Wang Z, Cheng M, Zhou L, Sun J (2008) Tetrahedron 64:11304–11312CrossRefGoogle Scholar
  190. 190.
    Ellman JA, Owens TD, Tang TP (2002) Acc Chem Res 35:984–995CrossRefGoogle Scholar
  191. 191.
    Fernandez I, Khiar N (2003) Chem Rev 103:3651–3705CrossRefGoogle Scholar
  192. 192.
    Ellman JA (2003) Pure Appl Chem 75:39–46CrossRefGoogle Scholar
  193. 193.
    Zhou P, Chen B-C, Davis FA (2004) Tetrahedron 60:8003–8030CrossRefGoogle Scholar
  194. 194.
    Senanayake CH, Krishnamurthy D, Lu Z-H, Han Z, Gallou I (2005) Aldrichim Acta 38:93–104Google Scholar
  195. 195.
    Morton D, Stockman RA (2006) Tetrahedron 62:8869–8905CrossRefGoogle Scholar
  196. 196.
    Pei D, Wang Z, Wei S, Zhang Y, Sun J (2006) Org Lett 8:5913–5915CrossRefGoogle Scholar
  197. 197.
    Pei D, Zhang Y, Wei S, Wang M, Sun J (2008) Adv Synth Catal 350:619–623CrossRefGoogle Scholar
  198. 198.
    Wang C, Wu X, Zhou L, Sun J (2008) Chem Eur J 14:8789–8792CrossRefGoogle Scholar
  199. 199.
    Liu X-W, Wang C, Yan Y, Wang Y-Q, Sun J (2013) J Org Chem 78:6276–6280CrossRefGoogle Scholar
  200. 200.
    Wang C, Wu X, Zhou L, Sun J (2015) Org Biomol Chem 13:577–582CrossRefGoogle Scholar
  201. 201.
    Benaglia M, Puglisi A, Cozzi F (2003) Chem Rev 103:3401–3429CrossRefGoogle Scholar
  202. 202.
    Cozzi F (2006) Adv Synth Catal 348:1367–1390CrossRefGoogle Scholar
  203. 203.
    Kristensen TE, Hansen T (2010) Eur J Org Chem, 3179–3204Google Scholar
  204. 204.
    Kristensen TE, Hansen T (2013) In: Dalko PI (ed) Comprehensive enantioselective organocatalysis. Wiley-VCH, Weinheim, pp 651–672CrossRefGoogle Scholar
  205. 205.
    Ge X, Qian C, Yea X, Chen X (2015) RSC Adv 5:65402–65407CrossRefGoogle Scholar
  206. 206.
    Malkov AV, Figlus M, Kočovský P (2008) J Org Chem 73:3985–3996CrossRefGoogle Scholar
  207. 207.
    Malkov AV, Figlus M, Prestly MR, Rabani G, Cooke G, Kočovský P (2009) Chem Eur J 15:9651–9654CrossRefGoogle Scholar
  208. 208.
    Malkov AV, Figlus M, Cooke G, Caldwell ST, Rabani G, Prestly MR, Kočovský P (2009) Org Biomol Chem 7:1878–1883CrossRefGoogle Scholar
  209. 209.
    Figlus M, Caldwell ST, Walas D, Yesilbag G, Cooke G, Kočovský P, Malkov AV, Sanyal A (2010) Org Biomol Chem 8:137–141CrossRefGoogle Scholar
  210. 210.
    Iwasaki F, Onomura O, Mishima K, Maki T, Matsumura Y (1999) Tetrahedron Lett 40:7507–7511CrossRefGoogle Scholar
  211. 211.
    Pini D, Iuliano A, Salvadori P (1992) Tetrahedron Asymmetry 3:693–694CrossRefGoogle Scholar
  212. 212.
    Schiffers R, Kagan HB (1997) Synlett, 1175–1178Google Scholar
  213. 213.
    LaRonde FJ, Brook MA (1999) Tetrahedron Lett 40:3507–3510CrossRefGoogle Scholar
  214. 214.
    Malkov AV, Liddon AJPS, Ramírez-López P, Bendová L, Haigh D, Kočovský P (2006) Angew Chem Int Ed 45:1432–1435CrossRefGoogle Scholar
  215. 215.
    Matsumura Y, Ogura K, Kouchi Y, Iwasaki F, Onomura O (2006) Org Lett 8:3789–3792CrossRefGoogle Scholar
  216. 216.
    Brown HC, Kulkarni SV, Racherla US (1994) J Org Chem 59:365–369CrossRefGoogle Scholar
  217. 217.
    Hilborn JW, Lu Z-H, Jurgens AR, Fang QK, Byers P, Wald SA, Senanayake CH (2001) Tetrahedron Lett 42:8919–8921CrossRefGoogle Scholar
  218. 218.
    Kamal A, Sandbhor M, Shaik AA (2003) Tetrahedron Asymmetry 14:1575–1580CrossRefGoogle Scholar
  219. 219.
    Steer DL, Lew RA, Perlmutter P, Smith AI, Aguilar M-I (2002) Curr Med Chem 9:811–822CrossRefGoogle Scholar
  220. 220.
    Juaristi E, Soloshonok VA (2005) Enantioselective synthesis of β-amino acids. Wiley-VCH, HobokenCrossRefGoogle Scholar
  221. 221.
    Sleebs BE, Van Nguyen TT, Hughes AB (2009) Org Prep Proced Int 41:429–478CrossRefGoogle Scholar
  222. 222.
    Weiner B, Szymański W, Janssen DB, Minnaard AJ, Feringa BL (2010) Chem Soc Rev 39:1656–1691CrossRefGoogle Scholar
  223. 223.
    Weickgenannt A, Oestreich M (2011) ChemCatChem 3:1527–1529CrossRefGoogle Scholar
  224. 224.
    Hsiao Y, Rivera NR, Rosner T, Krska SW, Njolito E, Wang F, Sun Y, Armstrong JD III, Grabowski EJJ, Tillyer RD, Spindler F, Malan C (2004) J Am Chem Soc 126:9918–9919CrossRefGoogle Scholar
  225. 225.
    Dai Q, Yang W, Zhang X (2005) Org Lett 7:5343–5345CrossRefGoogle Scholar
  226. 226.
    Zheng H-J, Chen W-B, Wu Z-J, Deng J-G, Lin W-Q, Yuan W-C, Zhang X-M (2008) Chem Eur J 14:9864–9867CrossRefGoogle Scholar
  227. 227.
    Jiang Y, Chen X, Zheng Y, Xue Z, Shu C, Yuan W, Zhang X (2011) Angew Chem Int Ed 50:7304–7307CrossRefGoogle Scholar
  228. 228.
    Bonsignore M, Benaglia M, Annunziata R, Celentano G (2011) Synlett, 1085–1088Google Scholar
  229. 229.
    Wu X, Li Y, Wang C, Zhou L, Lu X, Sun J (2011) Chem Eur J 17:2846–2848CrossRefGoogle Scholar
  230. 230.
    Sugiura M, Kumahara M, Nakajima M (2009) Chem Commun, 3585–3587Google Scholar
  231. 231.
    Guizzetti S, Benaglia M, Bonsignore M, Raimondi L (2011) Org Biomol Chem 9:739–743CrossRefGoogle Scholar
  232. 232.
    Xiao Y-C, Wang C, Yao Y, Sun J, Chen Y-C (2011) Angew Chem Int Ed 50:10661–10664CrossRefGoogle Scholar
  233. 233.
    Liu X-W, Yan Y, Wang Y-Q, Wang C, Sun J (2012) Chem Eur J 18:9204–9207CrossRefGoogle Scholar
  234. 234.
    Torssell S, Kienle M, Somfai P (2005) Angew Chem Int Ed 44:3096–3099CrossRefGoogle Scholar
  235. 235.
    Chrzanowska M, Dreas A (2006) Heterocycles 69:303–310CrossRefGoogle Scholar
  236. 236.
    Malkov AV, Stončius S, Vranková K, Arndt M, Kočovský P (2008) Chem Eur J 14:8082–8085CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Laboratorio de Organocatálisis Asimétrica. Instituto de Sintesis Química y Catálisis Homogénea (ISQCH-CSIC)SaragossaSpain

Personalised recommendations