Skip to main content
SpringerLink
Log in

Pd-Catalyzed Diastereoselective Carbocyanation Reactions of Chiral N-Allyl Carboxamides and Indoles

  • Chapter
  • First Online:
Stereoselective Heterocycle Synthesis via Alkene Difunctionalization

Part of the book series: Springer Theses ((Springer Theses))

  • 458 Accesses

Abstract

Although still in its early stages, the aryliodination reaction is a noteworthy transformation due to its ability to rapidly construct all-carbon quaternatry centers. Chapter 1 outlined key discoveries which facilitated a significant broadening of the reaction scope, and the first application of this methodology in the synthesis of a natural product.

Portions of this chapter have appeared in print. See Refs. [1, 2].

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 109.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 139.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 139.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Notes

  1. 1.

    References [3, 4].

  2. 2.

    Reference [5].

  3. 3.

    Although this reaction is referred to as the Rosenmund-von Braun reaction, Rosenmund contribution showed that ArX reacts with KCN, KOH and H2O in a CuCN promoted reaction leading to the benzoic acid derivatives. von Braun used this reaction, yet did not study it in detail or expand the scope. See Refs. [6,7,8,9].

  4. 4.

    Reference [10].

  5. 5.

    Reference [11].

  6. 6.

    References [9, 12].

  7. 7.

    Reference [13].

  8. 8.

    Reference [14].

  9. 9.

    Reference [15].

  10. 10.

    Reference [16].

  11. 11.

    Reference [17].

  12. 12.

    References [18, 19].

  13. 13.

    Reference [20].

  14. 14.

    Reference [21].

  15. 15.

    Reference [22].

  16. 16.

    Reference [23].

  17. 17.

    Reference [24].

  18. 18.

    Reference [25].

  19. 19.

    Reference [26].

  20. 20.

    References [27, 28].

  21. 21.

    Reference [29].

  22. 22.

    Reference [30].

  23. 23.

    References [31,32,33,34,35].

  24. 24.

    Reference [36].

  25. 25.

    References [37, 38].

  26. 26.

    Reference [39].

  27. 27.

    Reference [40].

  28. 28.

    References [41, 42].

  29. 29.

    Reference [43].

  30. 30.

    Reference [44].

  31. 31.

    Reference [45].

  32. 32.

    Reference [46].

  33. 33.

    Reference [47].

  34. 34.

    Reference [48].

  35. 35.

    Reference [49].

  36. 36.

    Reference [50].

  37. 37.

    Reference [51].

  38. 38.

    Around the same time, an intermolecular variant was reported. See Ref. [52].

  39. 39.

    References [53,54,55].

  40. 40.

    Reference [56].

  41. 41.

    References [57,58,59,60].

  42. 42.

    References [54, 61].

  43. 43.

    References [62, 63].

  44. 44.

    References [64, 65].

  45. 45.

    Reference [66].

  46. 46.

    Reference [67].

  47. 47.

    Reference [68].

  48. 48.

    Reference [69].

  49. 49.

    References [70, 71].

  50. 50.

    Reference [72].

  51. 51.

    Reference [73].

  52. 52.

    For an example of the addition of TMSCN across alkynes, see: Ref. [74].

  53. 53.

    Reference [75].

  54. 54.

    Reference [76].

  55. 55.

    Reference [77].

  56. 56.

    Reference [78].

  57. 57.

    References [79, 80].

  58. 58.

    Reference [81].

  59. 59.

    Reference [82].

  60. 60.

    Price taken from: http://www.strem.com/catalog/v/26-3575/32/iron_312959-24-3 on 04/18/2016.

  61. 61.

    Reference [83].

  62. 62.

    Reference [84].

  63. 63.

    Reference [85].

  64. 64.

    References [86,87,88,89].

  65. 65.

    Reference [55].

  66. 66.

    Reference [91].

  67. 67.

    Reference [92].

  68. 68.

    Reference [93].

  69. 69.

    Reference [94].

  70. 70.

    Reference [95].

  71. 71.

    Reference [96].

  72. 72.

    Dimethyl amine is a gas at ambient temperature and pressure with a boiling point of 7 °C. Dibutyl amine has a boiling point of 159 °C.

  73. 73.

    Reference [97].

  74. 74.

    Reference [98].

  75. 75.

    Reference [99].

  76. 76.

    Reference [100].

  77. 77.

    Reference [101].

  78. 78.

    Reference [102].

  79. 79.

    Reference [103].

  80. 80.

    Reference [104].

  81. 81.

    Reference [105].

  82. 82.

    Reference [106].

  83. 83.

    Reference [107].

  84. 84.

    Reference [108].

  85. 85.

    Reference [109].

  86. 86.

    Reference [110].

  87. 87.

    Reference [111].

  88. 88.

    Reference [112].

  89. 89.

    This compound was prepared by Hyung Yoon.

  90. 90.

    This compound was prepared by Hyung Yoon.

  91. 91.

    This compound was prepared by Hyung Yoon.

  92. 92.

    This compound was prepared by Hyung Yoon.

  93. 93.

    This compound was prepared by Hyung Yoon.

  94. 94.

    This compound was prepared by Hyung Yoon.

  95. 95.

    This compound was prepared by Hyung Yoon.

  96. 96.

    This compound was prepared by Hyung Yoon.

  97. 97.

    This compound was prepared by Hyung Yoon.

  98. 98.

    This compound was prepared by Hyung Yoon.

  99. 99.

    This compound was prepared by Hyung Yoon.

  100. 100.

    This compound was prepared by Hyung Yoon.

  101. 101.

    This compound was prepared by Hyung Yoon.

  102. 102.

    This compound was prepared by Hyung Yoon.

  103. 103.

    This compound was prepared by Hyung Yoon.

  104. 104.

    This compound was prepared by Hyung Yoon.

  105. 105.

    This compound was prepared by Hyung Yoon.

  106. 106.

    This compound was prepared by Hyung Yoon.

  107. 107.

    This compound was prepared by Hyung Yoon.

  108. 108.

    This compound was prepared by Hyung Yoon.

  109. 109.

    This compound was prepared by Hyung Yoon.

  110. 110.

    Reference [113].

  111. 111.

    Reference [114].

  112. 112.

    Reference [115].

  113. 113.

    Reference [116].

  114. 114.

    This compound was synthesized by Andy Yen.

  115. 115.

    This compound was synthesized by Andy Yen.

  116. 116.

    This compound was synthesized by Andy Yen.

  117. 117.

    This compound was synthesized by Andy Yen.

  118. 118.

    This compound was synthesized by Andy Yen.

  119. 119.

    This compound was synthesized by Nicolas Zeidan.

  120. 120.

    This compound was synthesized by Andy Yen.

  121. 121.

    This compound was synthesized by Andy Yen.

  122. 122.

    This compound was synthesized by Andy Yen.

  123. 123.

    This compound was synthesized by Andy Yen.

  124. 124.

    This compound was synthesized by Andy Yen.

  125. 125.

    This compound was synthesized by Andy Yen.

  126. 126.

    This compound was synthesized by Andy Yen.

  127. 127.

    This compound was synthesized by Andy Yen.

  128. 128.

    This compound was synthesized by Andy Yen.

  129. 129.

    This compound was synthesized by Nicolas Zeidan.

  130. 130.

    This compound was synthesized by Andy Yen.

  131. 131.

    This compound was synthesized by Andy Yen.

  132. 132.

    This compound was synthesized by Andy Yen.

  133. 133.

    This compound was synthesized by Andy Yen.

  134. 134.

    This compound was synthesized by Andy Yen.

  135. 135.

    This compound was synthesized by Andy Yen.

  136. 136.

    Reference [117].

References

  1. Yoon, H., Petrone, D.A., Lautens, M.: Org. Lett. 16, 6420 (2014)

    Article  CAS  Google Scholar 

  2. Petrone, D.A., Yen, A., Zeidan, N., Lautens, M.: Org. Lett. 17, 4838 (2015)

    Article  CAS  Google Scholar 

  3. Knah, N.-H., Kureshy, R.I., Abdi, S.H.R., Agarwal, S., Jasra, R.V.: Coor. Chem. Rev. 252, 593 (2008)

    Article  CAS  Google Scholar 

  4. Kurono, N., Ohkuma, T.: ACS. Catal. 6, 989 (2016)

    Article  CAS  Google Scholar 

  5. Pongratz, A.: Monatsh. Chem. 48, 585 (1927)

    Article  CAS  Google Scholar 

  6. Rosenmund, K.W., Struck, E.: Chem. Ber. 52, 1749 (1919)

    Article  Google Scholar 

  7. von Braun, J., Manz, G.: Liebigs Ann. Chem. 488, 111 (1931)

    Article  Google Scholar 

  8. Lindley, J.: Tetrahedron 40, 1433 (1984)

    Article  CAS  Google Scholar 

  9. Ellis, G.P., Romney-Alexander, T.M.: Chem. Rev. 87, 779 (1987)

    Article  CAS  Google Scholar 

  10. Beletskaya, I.P., Sigeev, A.S., Peregudov, A.S., Petrovskii, P.V.: J. Organomet. Chem. 689, 3810 (2004)

    Article  CAS  Google Scholar 

  11. Anbarasan, P., Schareina, T., Beller, M.: Chem. Soc. Rev. 40, 5049 (2011)

    Article  CAS  Google Scholar 

  12. Wen, Q., Jin, J., Zhang, L., Luo, L., Lu, P., Wang, Y.: Tetrahedron Lett. 55, 1271 (2014)

    Article  CAS  Google Scholar 

  13. Takagi, K., Okamoto, T., Sakakibara, Y.: Chem. Lett, 471 (1973)

    Google Scholar 

  14. Takagi, K., Okamoto, T., Sakakibara, Y., Ohno, A., Oka, S., Hayama, N.: Bull. Chem. Soc. Jpn 49, 3177 (1976)

    Article  CAS  Google Scholar 

  15. Cassar, L., Foà, M., Montanari, F., Marinelli, G.P.: J. Organomet. Chem. 173, 335 (1979)

    Article  CAS  Google Scholar 

  16. Takagi, K., Okamoto, T., Sakakibara, Y., Ohno, A., Oka, S., Hayama, N.: Bull. Chem. Soc. Jpn 48, 3298 (1975)

    Article  CAS  Google Scholar 

  17. Yamamura, K., Muzahashi, S.J.: Tetrahedron Lett. 18, 4429 (1977)

    Article  Google Scholar 

  18. Dalton, J.R., Regen, S.L.: J. Org. Chem. 44, 4443 (1979)

    Article  CAS  Google Scholar 

  19. Regen, S.L., Quici, S., Liaw, S.J.: J. Org. Chem. 44, 2029 (1979)

    Article  CAS  Google Scholar 

  20. Luo, F.-H., Chu, C.-I., Cheng, C.-H.: Organometallics 1998, 17 (1025)

    Google Scholar 

  21. Jiang, B., Kann, Y., Zangh, A.: Tetrahedron 57, 1581 (2001)

    Article  CAS  Google Scholar 

  22. Sundermeier, M., Zapf, A., Beller, M.: Eur. J. Inorg. Chem., 3513 (2003)

    Google Scholar 

  23. Jin, F., Confalone, P.N.: Tetrahedron Lett. 41, 3271 (2000)

    Article  CAS  Google Scholar 

  24. Zapf, A., Beller, M.: Chem. Eur. J. 7, 2908 (2001)

    Article  CAS  Google Scholar 

  25. Gómez Andreu, M., Zapf, A., Beller, M. Chem. Commun., 2475 (2000)

    Google Scholar 

  26. Ehrentraut, A., Zapf, A., Beller, M.J.: Mol. Catal. 182–183, 515 (2002)

    Article  Google Scholar 

  27. Sundermeier, M., Zapf, A., Beller, M.: Tetrahedron Lett. 42, 670 (2001)

    Article  Google Scholar 

  28. Sundermeier, M., Zapf, A., Mutyala, S., Baumann, W., Sans, J., Weiss, S., Beller, M.: Chem. Eur. J. 9, 1828 (2003)

    Article  CAS  Google Scholar 

  29. Littke, A., Soumeillant, M., Kaltenback, R.F., Cherney, R.J., Tarby, C.M., Kiau, S.: Org. Lett. 9, 1711 (2007)

    Article  CAS  Google Scholar 

  30. Shareina, T., Zapf, A., Beller, M.: Chem. Commmun., 1388 (2004)

    Google Scholar 

  31. Murahashi, S., Naota, T., Nakajima, N.: J. Org. Chem. 51, 898 (1986)

    Article  CAS  Google Scholar 

  32. Miller, J.A.: Tetrahedron Lett. 42, 6991 (2001)

    Article  CAS  Google Scholar 

  33. Miller, J.A., Dankwardt, J.W.: Tetrahedron Lett. 2003, 44 (1907)

    Google Scholar 

  34. Miller, J.A., Dankwardt, J.W., Penney, J.M.: Synthesis 11, 1643 (2003)

    Article  Google Scholar 

  35. Penney, J.M., Miller, J.A.: Tetrahedron Lett. 45, 4989 (2004)

    Article  CAS  Google Scholar 

  36. Nakao, Y., Hiyama, T.: Pure Appl. Chem. 2008, 80 (1097)

    Google Scholar 

  37. Nakao, Y., Oda, S., Hiyama, T.: J. Am. Chem. Soc. 126, 13904 (2004)

    Article  CAS  Google Scholar 

  38. Nakao, Y., Oda, S., Yada, A., Hiyama, T.: Tetrahedron Lett. 62, 7567 (2006)

    Article  CAS  Google Scholar 

  39. Nakao, Y., Yada, A., Ebata, S., Hiyama, T.: J. Am. Chem. Soc. 129, 2428 (2007)

    Article  CAS  Google Scholar 

  40. Nakao, Y., Yada, A., Satoh, J., Ebata, S., Oda, S., Hiyama, T.: Chem. Lett. 35, 790 (2006)

    Article  CAS  Google Scholar 

  41. Nakoa, Y., Yukawa, T., Hirata, Y., Oda, S., Satoh, J., Hiyama, T.: J. Am. Chem. Soc. 128, 7116 (2006)

    Article  CAS  Google Scholar 

  42. Hirata, Y., Yukawa, T., Kashihara, N., Nakao, Y., Yiyama, T.: J. Am. Chem. Soc. 131, 10964 (2009)

    Article  CAS  Google Scholar 

  43. Nakao, Y., Hirata, Y., Tanaka, M., Hiyama, T.: Angew. Chem. Int. Ed. 47, 385 (2008)

    Article  CAS  Google Scholar 

  44. Hirata, Y., Iniu, T., Nakao, Y., Hiyama, T.: J. Am. Chem. Soc. 131, 6642 (2009)

    Google Scholar 

  45. Hirata, Y., Yada, A., Morita, E., Nakao, Y., Hiyama, T., Ohashi, M., Ogoshi, S.: J. Am. Chem. Soc. 132, 10070 (2010)

    Article  CAS  Google Scholar 

  46. Nakao, Y., Yada, A., Hiyama, T.: J. Am. Chem. Soc. 132, 10024 (2010)

    Article  CAS  Google Scholar 

  47. Nakao, Y., Ebata, S., Yada, A., Hiyama, T., Ikawam, M., Ogoshi, S.: J. Am. Chem. Soc. 130, 12874 (2008)

    Article  CAS  Google Scholar 

  48. Hsieh, J.-C., Ebata, S., Nakao, Y., Hiyama, Y.: Synthesis 11, 1709 (2010)

    Google Scholar 

  49. Watson, M.P., Jacobsen, E.N.: J. Am. Chem. Soc. 130, 12594 (2008)

    Article  CAS  Google Scholar 

  50. Fang, X., Yu, P., Morandi, B.: Science 351, 832 (2016)

    Article  CAS  Google Scholar 

  51. Burns, B., Grigg, R., Sridharan, V., Worakun, T.: Tetrahedron Lett. 29, 4325 (1988)

    Article  CAS  Google Scholar 

  52. Arcadi, A., Bernocchi, E., Burini, A., Cacchi, S., Marinelle, F., Pietroni, B.: Tetrahedron 44, 481 (1988)

    Article  CAS  Google Scholar 

  53. Burns, B., Grigg, R., Santhakumar, V., Sridharan, V., Strevenson, P., Worakun, T.: Tetrahedron 48, 7297 (1992)

    Article  CAS  Google Scholar 

  54. Grigg, R., Sridharan, V.: J. Organomet. Chem. 576, 65 (1999)

    Article  CAS  Google Scholar 

  55. Brown, S., Clarkson, S., Grigg, R., Thomas, W.A., Sridharan, B., Wilson, D.M.: Tetrahedron 57, 1347 (2001)

    Article  CAS  Google Scholar 

  56. René, O., Lapoint, D., Fagnou, K.: Org. Lett. 11, 4560 (2009)

    Article  CAS  Google Scholar 

  57. Brown, D., Grigg, R., Sridhara, V., Tambyrajah, V.: Tetrahedron Lett. 36, 8137 (1995)

    Article  CAS  Google Scholar 

  58. Ruck, R.T., Huffman, M.A., Kim, M.M., Shelvin, M., Kandur, W.V., Davies, I.W.: Angew. Chem. Int. Ed. 47, 4711 (2008)

    Article  CAS  Google Scholar 

  59. Satyanarayana, G., Maichle-Mössmer, C., Maier, M.E.: Chem. Commun. 12, 1571 (2009)

    Article  CAS  Google Scholar 

  60. Hu, Y., Yu, C., Ren, D., Hu, Q., Zhang, L., Cheng, D.: Angew. Chem. Int. Ed. 48, 5448 (2009)

    Article  CAS  Google Scholar 

  61. Jaegli, S., Erb, W., Retailleau, P., Vors, J.-P., Neuville, L., Zhu, J.: Chem. Eur. J. 16, 5863 (2010)

    Article  CAS  Google Scholar 

  62. Liu, X., Ma, X., Huang, Y., Gu, Z.: Org. Lett. 15, 4814 (2013)

    Article  CAS  Google Scholar 

  63. Liu, Z., Xia, Y., Zhou, S., Wang, L., Zhang, Y., Wang, J.: Org. Lett. 15, 5032 (2013)

    Article  CAS  Google Scholar 

  64. Vachhani, D.D., Butani, H.H., Sharma, N., Bhoya, U.C., Shah, A.K., Van der Eycken, E.V.: Chem. Commun. 51, 14862 (2015)

    Article  CAS  Google Scholar 

  65. Yoon, H., Jang, Y.-J., Lautens, M.: Synthesis 48, 1483 (2016)

    Article  CAS  Google Scholar 

  66. Nájera, C., Sansano, J.M.: Angew. Chem. Int. Ed. 48, 2452 (2009)

    Article  CAS  Google Scholar 

  67. Torii, S., Okumoto, H., Ozaki, H., Nakayasu, S., Tadokoro, T., Kotani, T.: Tetrahedron Lett. 33, 3499 (1992)

    Article  CAS  Google Scholar 

  68. Grigg, R., Santhakumar, V., Sridharan, V.: Tetrahedron Lett. 34, 3163 (1993)

    Article  CAS  Google Scholar 

  69. Pinto, A., Jia, Y., Leuville, L., Zhu, J.: Chem. Eur. J. 13, 961 (2007)

    Article  CAS  Google Scholar 

  70. Jaegli, S., Vors, J.-P., Leuville, L., Zhu, J.: Synlett 18, 2997 (2009)

    Google Scholar 

  71. Jaegli, S., Vors, J.-P., Leuville, L., Zhu, J.: Tetrahedron 66, 8911 (2010)

    Article  CAS  Google Scholar 

  72. Lee, H.S., Kim, K.H., Lim, J.W., Kim, J.N.: Bull. Chem. Soc. Jpn 2011, 32 (1082)

    Google Scholar 

  73. Lu, Z., Hu, C., Guo, J., Li, J., Zui, Y., Jia, Y.: Org. Lett. 12, 280 (2010)

    Article  CAS  Google Scholar 

  74. Chatani, N., Takeyasu, T., Noriuchi, N., Hanafusa, T.: J. Org. Chem. 53, 3539 (1988)

    Article  CAS  Google Scholar 

  75. Nozaki, K., Sato, N., Takaya, H.: J. Org. Chem. 59, 2679 (1994)

    Article  CAS  Google Scholar 

  76. Nozaki, K., Sato, N., Takaya, H.: Bull. Chem. Soc. Jpn 69, 1629 (1996)

    Article  CAS  Google Scholar 

  77. Nishihara, Y., Inoue, Y., Itazaki, M., Takagi, K.: Org. Lett. 7, 2639 (2005)

    Article  CAS  Google Scholar 

  78. Nishihara, Y., Inoue, Y., Izawa, S., Miyasaka, M., Tanemure, K., Nakajima, K., Takagi, K.: Tetrahedron 62, 9872 (2006)

    Article  CAS  Google Scholar 

  79. Kobayashi, Y., Kamisaki, H., Yanada, R., Takemoto, Y.: Org. Lett. 8, 2711 (2006)

    Article  CAS  Google Scholar 

  80. Kobayashi, Y., Kamisaki, H., Takeda, H., Yasui, Y., Yanada, R., Takemoto, Y.: Tetrahedron 63, 2978 (2007)

    Article  CAS  Google Scholar 

  81. Kobayashi, Y., Kamisaki, H., Takemoto, Y.: Org. Lett. 10, 3303 (2008)

    Article  CAS  Google Scholar 

  82. Cheng, Y.-N., Duan, Z., Yu, L., Li, Z., Zhu, Y., Wu, Y.: Org. Lett. 10, 901 (2008)

    Article  CAS  Google Scholar 

  83. Hopkins, C.R., O’Neil, S.V., Laufersweiler, M.C., Wang, Y., Pokross, M., Mekel, M., Evdokimov, A., Walter, R., Kontoyianni, M., Petrey, M.E., Sabatakos, G., Roesgen, J.T., Richardson, E., Demuth, T.P.: Bioorg. Med. Chem. Lett. 16, 5659 (2006)

    Article  CAS  Google Scholar 

  84. Schareina, T., Zapf, A., Beller, M.: J. Organomet. Chem. 689, 4576 (2004)

    Article  CAS  Google Scholar 

  85. Tschaen, D.M., Desmond, R., King, A.O., Fortin, M.C., Pipik, B., King, S., Verhoeven, T.R.: Synth. Commun. 24, 887 (1994)

    Article  CAS  Google Scholar 

  86. Venkatraman, S., Li, C.-J.: Org. Lett. 1, 1133 (1999)

    Article  CAS  Google Scholar 

  87. Venkatraman, S., Li, C.-J.: Tetrahedron Lett. 41, 4831 (2000)

    Article  CAS  Google Scholar 

  88. Li, J.-H., Xie, Y.-X., Yin, D.-L.: J. Org. Chem. 68, 9867 (2003)

    Article  CAS  Google Scholar 

  89. Wang, L., Zhang, Y., Liu, L., Wang, Y.: J. Org. Chem. 71, 1284 (2006)

    Article  CAS  Google Scholar 

  90. Littke, A.F., Fu, G.C.: J. Am. Chem. Soc. 123, 6989 (2001)

    Article  CAS  Google Scholar 

  91. Zhao, L., Li, Z., Chang, L., Xu, J., Yao, H., Wu, X.: Org. Lett. 14, 2066 (2012)

    Article  CAS  Google Scholar 

  92. Shen, C., Liu, R.-R., Fan, R.-J., Li, Y.-L., Xu, T.-F., Gao, J.-R., Jia, Y.-X.: J. Am. Chem. Soc. 137, 4936–4939 (2015)

    Article  CAS  Google Scholar 

  93. Hastings, D.J., Weedon, A.C.: Can. J. Chem. 69, 1171 (1991)

    Article  CAS  Google Scholar 

  94. Fang, Y.-Q., Lautens, M.: Org. Lett. 7, 3549 (2005)

    Article  CAS  Google Scholar 

  95. Negishi, E.-I., Coperet, C., Ma, S., Liou, S.-Y., Liu, F.: Chem. Rev. 96, 365 (1996)

    Article  CAS  Google Scholar 

  96. Bipp, H., Kieczka, H.: Formamides. In: Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim (2010)

    Google Scholar 

  97. Weinstein, A.B., Stahl, S.S.: Catal. Sci. Technol. 4, 4301 (2014)

    Article  CAS  Google Scholar 

  98. Kozikowski, A.P., Ma, D.: Tetrahedron Lett. 32, 3317 (1991)

    Article  CAS  Google Scholar 

  99. Freerksen, R.W., Selikson, S.J., Wroble, R.R., Kyler, K.S., Watt, D.S.: J. Org. Chem. 48, 4087 (1983)

    Article  CAS  Google Scholar 

  100. Davis, F.A., Nadir, U.K.: Tetrahedron Lett. 18, 1721 (1977)

    Article  Google Scholar 

  101. Petrone, D.A., Yoon, H., Weinstabl, H., Lautens, M.: Angew. Chem. Int. Ed. 53, 7908 (2014)

    Article  CAS  Google Scholar 

  102. Fang, Y.-Q., Lautens, M.: J. Org. Chem. 73, 538 (2008)

    Article  CAS  Google Scholar 

  103. Basset, J., Romero, M., Serra, T., Pujol, M.D.: Tetrahedron 68, 356 (2012)

    Article  CAS  Google Scholar 

  104. Stokes, B.J., Dong, H., Leslie, B.E., Pumphrew, A.L., Driver, T.G.: J. Am. Chem. Soc. 129, 7500 (2007)

    Article  CAS  Google Scholar 

  105. Weinstabl, H., Suhartono, M., Qureshi, Z., Lautens, M.: Angew. Chem. Int. Ed. 52, 5305 (2013)

    Article  CAS  Google Scholar 

  106. Lian, J.-J., Odedra, A., Wu, C.-J., Liu, R.S.: J. Am. Chem. Soc. 127, 4186 (2005)

    Article  CAS  Google Scholar 

  107. Karaki, F., Ohgane, K., Fukuda, H., Nakamura, M., Dodo, K., Hashimoto, Y.: Bioorg. Med. Chem. 22, 3587 (2014)

    Article  CAS  Google Scholar 

  108. Suresh, R.R., Kumara Swamy, K.C.: J. Org. Chem. 77, 6959 (2012)

    Article  CAS  Google Scholar 

  109. Ferraccioli, R., Carenzi, D., Motti, E., Catellani, M.: J. Am. Chem. Soc. 128, 722 (2006)

    Article  CAS  Google Scholar 

  110. Axford, L.C., Holden, K.E., Hasse, K., Banwell, M.G., Steglich, W., Wagler, J., Willis, A.C.: Aust. J. Chem. 61, 80 (2008)

    Article  CAS  Google Scholar 

  111. Barton, T.J., Lin, J., Ijadi-Maghsoodi, S., Power, M.D., Zhang, X., Ma, Z., Shimizu, H., Gordon, M.S.: J. Am. Chem. Soc. 117, 11695 (1995)

    Article  CAS  Google Scholar 

  112. Bunch, L., Jensen, A.A., Nielsen, B., Braeuner-Osborn, H.: J. Med. Chem. 49, 172 (2006)

    Article  CAS  Google Scholar 

  113. Yamagishi, M., Nishigai, K., Ishii, A., Hata, T., Urabe, H.: Angew. Chem. Int. Ed. 51, 6471–6474 (2012)

    Article  CAS  Google Scholar 

  114. Mosley, C.A., Myers, S.J., Murray, E.E., Santangelo, R., Tahirovic, Y.A., Kurtkaya, N., Mullasseril, P., Yuan, H., Lyuboslavsky, P., Le, P., Wilson, L.J., Yepes, M., Dingledine, R., Traynelis, S.F., Liotta, D.C.: Bioog. Med. Chem. 17, 6463 (2009)

    Article  CAS  Google Scholar 

  115. Wang, Y., Ye, L., Zhang, L.: Chem. Commun. 47, 7815 (2011)

    Article  CAS  Google Scholar 

  116. Ito, Y., Kobayashi, K., Seko, N., Saegusa, T.: Bull. Chem. Soc. Jpn 57, 73 (1984)

    Article  CAS  Google Scholar 

  117. Vishwakarma, L.C., Stringer, O.D., Davis, F.A.: Org. Syn. 66, 203 (1988)

    Article  CAS  Google Scholar 

Download references

Author information

Author notes

  1. David A. Petrone

    Present address: Laboratory for Organic Chemistry, ETH Zürich, Zürich, Switzerland

Authors and Affiliations

    Authors
    1. David A. Petrone
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding author

    Correspondence to David A. Petrone .

    Rights and permissions

    Reprints and permissions

    Copyright information

    © 2018 Springer International Publishing AG, part of Springer Nature

    About this chapter

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this chapter

    Petrone, D.A. (2018). Pd-Catalyzed Diastereoselective Carbocyanation Reactions of Chiral N-Allyl Carboxamides and Indoles. In: Stereoselective Heterocycle Synthesis via Alkene Difunctionalization. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-77507-4_2

    Download citation

    Publish with us

    Policies and ethics

    Search

    Navigation