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CO2-Mediated Formation of Chiral Fine Chemicals

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Carbon Dioxide and Organometallics

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 53))

Abstract

The utilization of carbon dioxide as a feedstock for the synthesis of organic chemicals can contribute to a more sustainable chemical industry, since CO2 is an abundant, inexpensive, and nontoxic renewable C1 resource. Nevertheless, far less attention was paid to the stereochemically controlled catalytic CO2 fixation/conversion processes. This review therefore aims to principally showcase the recent progress regarding CO2-mediated formation of chiral fine chemicals, including enantioselective synthesis of cyclic carbonates by asymmetric ring opening of epoxides with CO2, enantioselective synthesis of oxazolidinones by the coupling reaction of aziridines with CO2- or base-mediated formation of oxazolidinone from ethanolamines, metal-catalyzed enantioselective synthesis of functional carboxylic acids and derivatives, and enantioselective synthesis of CO2-based polycarbonates from epoxides.

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References

  1. Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107:2365

    Article  CAS  Google Scholar 

  2. Darensbourg DJ (2010) Inorg Chem 49:10765

    Article  CAS  Google Scholar 

  3. Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kühn FE (2011) Angew Chem Int Ed 50:8510

    Article  CAS  Google Scholar 

  4. He MY, Sun YH, Han BX (2013) Angew Chem Int Ed 52:9620

    Article  CAS  Google Scholar 

  5. Aresta M, Dibenedetto A (2007) Dalton Trans 28:2975

    Article  Google Scholar 

  6. Lu XB, Darensbourg DJ (2012) Chem Soc Rev 41:1462

    Article  CAS  Google Scholar 

  7. Kielland N, Whiteoak CJ, Kleij AW (2013) Adv Synth Catal 355:2115

    Article  CAS  Google Scholar 

  8. Ian Childers M, Longo JM, Van Zee NJ, LaPointe AM, Coates GW (2014) Chem Rev 114:8129

    Article  Google Scholar 

  9. Burk RM, Roof MB (1993) Tetrahedron Lett 34:395

    Article  CAS  Google Scholar 

  10. Hisch H, Millini R, Wang IJ (1986) Chem Ber 119:1090

    Article  Google Scholar 

  11. Matsumoto K, Fuwa S, Kitajima H (1995) Tetrahedron Lett 36:6499

    Article  CAS  Google Scholar 

  12. Shimojo M, Matsumoto K, Hatanaka M (2000) Tetrahedron 56:9281

    Article  CAS  Google Scholar 

  13. Trost BM, Angle SR (1985) J Am Chem Soc 107:6123

    Article  CAS  Google Scholar 

  14. Gendre PL, Braun T, Bruneau C, Dixneuf PH (1996) J Org Chem 61:8453

    Article  Google Scholar 

  15. Li B, Wu GP, Ren WM, Wang YM, Lu XB (2008) J Polym Sci A Polym Chem 46:6102

    Article  CAS  Google Scholar 

  16. Aresta M, Dibenedetto A, Gianfrate L, Pastore C (2003) Appl Catal A Gen 255:5

    Article  CAS  Google Scholar 

  17. Zhang X, Jia YB, Lu XB, Li B, Wang H, Sun LC (2008) Tetrahedron Lett 49:6589

    Article  CAS  Google Scholar 

  18. Ren WM, Liu Y, Lu XB (2014) J Org Chem 79:9771

    Article  CAS  Google Scholar 

  19. Jacobsen EN (2000) Acc Chem Res 33:421

    Article  CAS  Google Scholar 

  20. Lu XB, Liang B, Zhang YJ, Tian YZ, Wang YM, Bai CX, Wang H, Zhang R (2004) J Am Chem Soc 126:3732

    Article  CAS  Google Scholar 

  21. Paddock RL, Nguyen ST (2004) Chem Commun 1622

    Google Scholar 

  22. Berkessel A, Brandenburg M (2006) Org Lett 8:4401

    Google Scholar 

  23. Chang T, Jing HW, Jin L, Qiu WY (2007) J Mol Catal A Chem 264:241

    Article  CAS  Google Scholar 

  24. Chang T, Jin L, Jing HW (2009) ChemCatChem 1:379

    Article  CAS  Google Scholar 

  25. Jin L, Huang Y, Jing HW, Chang T, Yan P (2008) Tetrahedron Asymmetry 19:1947

    Google Scholar 

  26. Zhang S, Song Y, Jing HW, Yan P, Cai Q (2009) Chin J Catal 30:1255

    Article  CAS  Google Scholar 

  27. Zhang S, Huang Y, Jing HW, Yao W, Yan P (2009) Green Chem 11:935

    Article  Google Scholar 

  28. Yan P, Jing HW (2009) Adv Synth Catal 351:13

    Google Scholar 

  29. Ren WM, Wu GP, Lin F, Jian JY, Liu C, Luo Y, Lu XB (2012) Chem Sci 3:2094

    Article  CAS  Google Scholar 

  30. Chen SW, Kawthekar RB, Kim GJ (2007) Tetrahedron Lett 48:297

    Google Scholar 

  31. Tanaka H, Kitaichi Y, Sato M, Ikeno T, Yamada T (2004) Chem Lett 676

    Google Scholar 

  32. Yoshida S, Fukui K, Kikuchi S, Yamada T (2010) J Am Chem Soc 132:4072

    Article  CAS  Google Scholar 

  33. Wouters J (1998) Curr Med Chem 5:137

    CAS  Google Scholar 

  34. Evans DA, Kim AS (1999) In: Coates RM, Denmark SE (eds) Handbook of reagents for organic synthesis: reagents, auxiliaries and catalysts for C–C bonds. Wiley, New York, pp 91–101

    Google Scholar 

  35. Du Y, Wu Y, Liu AH, He LN (2008) J Org Chem 73:4709

    Article  CAS  Google Scholar 

  36. Seayad J, Seayad AM, Ng JKP, Chai CLL (2012) ChemCatChem 4:774

    Article  CAS  Google Scholar 

  37. Feroci M, Gennaro A, Inesi A, Orsini M, Palombi L (2002) Tetrahedron Lett 43:5863

    Article  CAS  Google Scholar 

  38. Casadei MA, Feroci M, Inesi A, Rossi L, Sotgiu G (2000) J Org Chem 65:4759

    Google Scholar 

  39. Foo SW, Takada Y, Yamazaki Y, Saito S (2013) Tetrahedron Lett 54:4717

    Article  CAS  Google Scholar 

  40. Paz J, Pérez-Balado C, Iglesias B, Muñoz L (2009) Synlett 3:395

    Google Scholar 

  41. Zhang K, Wang H, Zhao SF, Niu DF, Lu JX (2009) J Electroanal Chem 630:35

    Article  CAS  Google Scholar 

  42. Chen BL, Tu ZY, Zhu HW, Sun WW, Wang H, Lu JX (2014) Electrochim Acta 116:475

    Article  CAS  Google Scholar 

  43. Takimoto M, Mori M (2002) J Am Chem Soc 124:10008

    Article  CAS  Google Scholar 

  44. Takimoto M, Nakamura Y, Kimura K, Mori M (2004) J Am Chem Soc 126:5956

    Article  CAS  Google Scholar 

  45. Zheng SC, Zhang M, Zhao XM (2014) Eur Chem J 20:7216

    Article  CAS  Google Scholar 

  46. Zhang M, Zhao XM, Zheng SC (2014) Chem Commun 50:4455

    Article  CAS  Google Scholar 

  47. Mita T, Sugawara M, Saito K, Sato Y (2014) Org Lett 16:3028

    Article  CAS  Google Scholar 

  48. Inoue S, Koinuma H, Tsuruta T (1969) J Polym Sci B Polym Lett 7:287

    Article  CAS  Google Scholar 

  49. Darensbourg DJ (2007) Chem Rev 107:2388

    Article  CAS  Google Scholar 

  50. Coates GW, Moore DR (2004) Angew Chem Int Ed 43:6618

    Article  CAS  Google Scholar 

  51. Qin ZQ, Thomas CM, Lee S, Coates GW (2003) Angew Chem Int Ed 42:5484

    Article  CAS  Google Scholar 

  52. Lu XB, Wang Y (2004) Angew Chem Int Ed 43:3574

    Article  CAS  Google Scholar 

  53. Lu XB, Shi L, Wang YM, Zhang R, Zhang YJ, Peng XJ, Zhang ZC, Li B (2006) J Am Chem Soc 128:1664

    Article  CAS  Google Scholar 

  54. Ren WM, Liu ZW, Wen YQ, Zhang R, Lu XB (2009) J Am Chem Soc 131:11509

    Article  CAS  Google Scholar 

  55. Ren WM, Zhang WZ, Lu XB (2010) Sci Chin Chem 53:1646

    Article  CAS  Google Scholar 

  56. Ren WM, Liu Y, Wu GP, Liu J, Lu XB (2011) J Polym Sci A Polym Lett 49:4894

    Article  CAS  Google Scholar 

  57. Wu GP, Wei SH, Lu XB, Ren WM, Darensbourg DJ (2010) Macromolecules 43:9202

    Article  CAS  Google Scholar 

  58. Wu GP, Wei SH, Ren WM, Lu XB, Li B, Zu YP, Darensbourg DJ (2011) Energy Environ Sci 4:5084

    Article  CAS  Google Scholar 

  59. Wu GP, Wei SH, Ren WM, Lu XB, Xu TQ, Darensbourg DJ (2011) J Am Chem Soc 133:15191

    Article  CAS  Google Scholar 

  60. Wu GP, Xu PX, Lu XB, Zu YP, Wei SH, Ren WM, Darensbourg DJ (2013) Macromolecules 46:2128

    Article  CAS  Google Scholar 

  61. Zhang H, Grinstaff MW (2013) J Am Chem Soc 135:6806

    Article  CAS  Google Scholar 

  62. Ren WM, Liang MW, Xu YC, Lu XB (2013) Polym Chem 4:4425

    Article  CAS  Google Scholar 

  63. Jacobsen EN, Wu MH (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, vol I–III. Springer, Berlin, pp 1309–1312

    Chapter  Google Scholar 

  64. Nozaki K, Nakano K, Hiyama T (1999) J Am Chem Soc 121:11008

    Article  CAS  Google Scholar 

  65. Nakano K, Nozaki K, Hiyama T (2003) J Am Chem Soc 125:5501

    Article  CAS  Google Scholar 

  66. Cheng M, Darling NA, Lobkovsky EB, Coates GW (2000) Chem Commun 2007

    Google Scholar 

  67. Xiao Y, Wang Z, Ding K (2005) Chem Eur J 11:3668

    Article  CAS  Google Scholar 

  68. Hua YZ, Lu LJ, Huang PJ, Wei DH, Tang MS, Wang MC, Chang JB (2014) Chem Eur J 20:12394

    Article  CAS  Google Scholar 

  69. Ellis WC, Jung Y, Mulzer M, Di Girolamo R, Lobkovsky EB, Coates GW (2014) Chem Sci 5:4004

    Article  CAS  Google Scholar 

  70. Abbina S, Du GD (2012) Organometallics 31:7394

    Article  CAS  Google Scholar 

  71. Nishioka K, Goto H, Sugimoto H (2012) Macromolecules 45:8172

    Article  CAS  Google Scholar 

  72. Lu XB, Ren WM, Wu GP (2012) Acc Chem Res 45:1721

    Article  CAS  Google Scholar 

  73. Shi L, Lu XB, Zhang R, Peng XJ, Zhang CQ, Li JF, Peng XM (2006) Macromolecules 39:5679

    Article  CAS  Google Scholar 

  74. Wu GP, Ren WM, Luo Y, Li B, Zhang WZ, Lu XB (2012) J Am Chem Soc 134:5682

    Article  CAS  Google Scholar 

  75. Wu GP, Jiang SD, Lu XB, Ren WM, Yan SK (2012) Chin J Polym Sci 30:487

    Article  CAS  Google Scholar 

  76. Liu Y, Ren WM, Liu J, Lu XB (2013) Angew Chem Int Ed 52:11594

    Article  CAS  Google Scholar 

  77. Liu Y, Ren WM, Liu C, Fu S, Wang M, He KK, Li RR, Zhang R, Lu XB (2014) Macromolecules 47:7775

    Article  CAS  Google Scholar 

  78. Liu Y, Ren WM, He KK, Lu XB (2014) Nat Commun 5:5687

    Article  CAS  Google Scholar 

  79. Liu Y, Wang M, Ren WM, He KK, Xu YC, Liu J, Lu XB (2014) Macromolecules 47:1269

    Article  CAS  Google Scholar 

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Acknowledgments

This work is supported by the National Natural Science Foundation of China (NSFC, Grant 21134002) and Program for Changjiang Scholars and Innovative Research Team in University (IRT13008). X. B. Lu gratefully acknowledges the Changjiang Scholars Program (T2011056) from the Ministry of Education of China.

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  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, China

    Xiao-Bing Lu

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  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China

    Xiao-Bing Lu

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Lu, XB. (2015). CO2-Mediated Formation of Chiral Fine Chemicals. In: Lu, XB. (eds) Carbon Dioxide and Organometallics. Topics in Organometallic Chemistry, vol 53. Springer, Cham. https://doi.org/10.1007/3418_2015_98

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