Chiral Amines Derived from Asymmetric Aza-Morita-Baylis-Hillman Reaction

Chiral Amine Synthesis: Methods, Developments and Applications

Volumn , Issue , 2010, Pages 397-430

  Dai, Lun zhi ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amines; Benzenesulfonamide; Boc protection; Carbenes; Detosylation; Enolate; Phosphines

Indexed keywords

EID: 84886319127     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527629541.ch13     Document Type: Chapter

References (90)

1. Bloch, R. (1998) Chem. Rev., 98, 1407-1438
2. Kobayashi, S. and Ishitani, H. (1999) Chem. Rev., 99, 1069-1094.
3. Kleinman, E.F. (1991) Chapter 4, in Comprehensive Organic Synthesis, vol. 2 (eds B.M. Trost and I. Fleming), Pergamon Press, Oxford, p. 893
4. Trost, B.M. and Fleming, I. (eds) (1991) Chapter 1, in Comprehensive Organic Synthesis, vol. 8, Pergamon Press, Oxford.
5. Morita, K., Suzuki, Z., and Hirose, H. (1968) Bull. Chem. Soc. Jpn., 41, 2815
6. Baylis, A.B. and Hillman, M.E.D. (1972) Offenlegungsschrift 2155113. U.S. Patent 3,743,669; Chem. Abstr. 77 (1972) 34174q.
7. Perlmutter, P. and Teo, C.C. (1984) Tetrahedron Lett., 25, 5951-5952
8. Basavaiah, D., Rao, A.J., and Satyanarayana, T. (2003) Chem. Rev., 103, 811-891
9. Masson, G., Housseman, C., and Zhu, J. (2007) Angew. Chem., Int. Ed., 46, 4614-4628
10. Basavaiah, D., Rao, K.V., and Reddy, R.J. (2007) Chem. Soc. Rev., 36, 1581-1588
11. Shi, Y.-L. and Shi, M. (2007) Eur. J. Org. Chem., 2905-2916
12. Singh, V. and Batra, S. (2008) Tetrahedron, 64, 4511-4574.
13. Hill, J.S. and Isaacs, N.S. (1990) J. Phys. Org. Chem., 3, 285-288
14. Bode, M.L. and Kaye, P.T. (1991) Tetrahedron Lett., 32, 5611-5614
15. Santos, L.S., Pavam, C.H., Almeida, W.P., Coelho, F., and Eberlin, M.N. (2004) Angew. Chem., Int. Ed., 43, 4330-4333.
16. Price, K.E., Broadwater, S.J., Jung, H.M., and McQuade, D.T. (2005) Org. Lett., 7, 147-150
17. Price, K.E., Broadwater, S.J., Walker, B.J., and McQuade, D.T. (2005) J. Org. Chem., 70, 3980-3987.
18. Augé, J., Lubin, N., and Lubineau, A. (1994) Tetrahedron Lett., 35, 7947-7948
19. Aggarwal, V.K., Dean, D.K., Mereu, A., and Williams, R. (2002) J. Org. Chem., 67, 510-514
20. Cai, J., Zhou, Z., Zhao, G., and Tang, C. (2002) Org. Lett., 4, 4723-4725
21. Yu, C., Liu, B., and Hu, L. (2001) J. Org. Chem., 66, 5413-5418
22. Yamada, Y.M.A. and Ikegami, S. (2000) Tetrahedron Lett., 41, 2165-2169
23. McDougal, N.T. and Schaus, S.E. (2003) J. Am. Chem. Soc., 125, 12094-12095.
24. Aggarwal, V.K., Fulford, S.Y., and Lloyd-Jones, G.C. (2005) Angew. Chem., Int. Ed., 44, 1706-1708
25. Robiette, R., Aggarwal, V.K., and Harvey, J.N. (2007) J. Am. Chem. Soc., 129, 15513-15525.
26. Raheem, I.T. and Jacobsen, E.N. (2005) Adv. Synth. Catal., 347, 1701-1708.
27. Buskens, P., Klankermayer, J., and Leitner, W. (2005) J. Am. Chem. Soc., 127, 16762-16763.
28. Iwabuchi, Y., Nakatani, M., Yokoyama, N., and Hatakeyama, S. (1999) J. Am. Chem. Soc., 121, 10219-10220
29. Iwabuchi, Y. and Hatakeyama, S. (2002) J. Synth. Org. Chem. Jpn., 60, 2-14.
30. Kündig, E.P., Xu, L.H., and Schnell, B. (1994) Synlett, 413-414.
31. Aggarwal, V.K., Castro, A.M.M., Mereu, A., and Adams, H. (2002) Tetrahedron Lett., 43, 1577-1581.
32. Shi, M. and Xu, Y.-M. (2002) Tetrahedron: Asymmetry, 13, 1195-1200.
33. Lu, A., Xu, X., Gao, P., Zhou, Z., Song, H., and Tang, C. (2008) Tetrahedron: Asymmetry, 19, 1886-1890.
34. Shi, M. and Xu, Y.-M. (2002) Angew. Chem., Int. Ed., 41, 4507-4510.
35. Shi, M., Xu, Y.-M., and Shi, Y.-L. (2005) Chem. Eur. J., 11, 1794-1802.
36. Shi, M., Qi, M.-J., and Liu, X.-G. (2008) Chem. Commun., 6025-6027.
37. Balan, D. and Adolfsson, H. (2003) Tetrahedron Lett., 44, 2521-2524.
38. Kawahara, S., Nakano, A., Esumi, T., Iwabuchi, Y., and Hatakeyama, S. (2003) Org. Lett., 5, 3103-3105.
39. Abermil, N., Masson, G., and Zhu, J. (2008) J. Am. Chem. Soc., 130, 12596-12597.
40. Matsui, K., Takizawa, S., and Sasai, H. (2005) J. Am. Chem. Soc., 127, 3680-3681.
41. Matsui, K., Tanaka, K., Horii, A., Takizawa, S., and Sasai, H. (2006) Tetrahedron: Asymmetry, 17, 578-583.
42. Roth, F., Gygax, P., and Frator, G. (1992) Tetrahedron Lett., 33, 1045-1048
43. Hayase, T., Shibata, T., Soai, K., and Wakatsuki, Y. (1998) Chem. Commun., 1271-1272
44. Li, W., Zhang, Z., Xiao, D., and Zhang, X. (2000) J. Org. Chem., 65, 3489-3496
45. Pereira, S.I., Adrio, J., Silva, A.M.S., and Carretero, J.C. (2005) J. Org. Chem., 70, 10175-10177.
46. Shi, M. and Chen, L.-H. (2003) Chem. Commun., 1310-1311
47. Shi, M., Chen, L.-H., and Li, C.-Q. (2005) J. Am. Chem. Soc., 127, 3790-3800
48. Shi, M., Ma, G.-N., and Gao, J. (2007) J. Org. Chem., 72, 9779-9781.
49. Shi, M. and Zhao, G.-L. (2004) Adv. Synth. Catal., 346, 1205-1219.
50. Buskens, P., Klankermayer, J., and Leitner, W. (2005) J. Am. Chem. Soc., 127, 16762-16763.
51. Shi, M. and Li, C.-Q. (2005) Tetrahedron: Asymmetry, 16, 1385-1391.
52. Lei, Z.-Y., Ma, G.-N., and Shi, M. (2008) Eur. J. Org. Chem., 3817-3820.
53. Matsui, K., Takizawa, S., and Sasai, H. (2006) Synlett, 761-765.
54. Shi, M., Chen, L.-H., and Teng, W.-D. (2005) Adv. Synth. Catal., 347, 1781-1789.
55. Liu, Y.-H., Chen, L.-H., and Shi, M. (2006) Adv. Synth. Catal., 348, 973-979.
56. Liu, Y.-H. and Shi, M. (2008) Adv. Synth. Catal., 350, 122-128.
57. Shi, Y.-L. and Shi, M. (2007) Adv. Synth. Catal., 349, 2129-2135.
58. Qi, M.-J., Ai, T., Shi, M., and Li, G. (2008) Tetrahedron, 64, 1181-1186
59. Guan, X.-Y., Jiang, Y.-Q., and Shi, M. (2008) Eur. J. Org. Chem., 2150-2155.
60. Garnier, J.-M., Anstiss, C., and Liu, F. (2009) Adv. Synth. Catal., 351, 331-338
61. Garnier, J.-M. and Liu, F. (2009) Org. Biomol. Chem., 7, 1272-1275.
62. Sheehan, J.C. and Hunneman, D.H. (1966) J. Am. Chem. Soc., 88, 3666-3667.
63. Knight, R.L. and Leeper, F.J. (1997) Tetrahedron Lett., 38, 3611-3614
64. Knight, R.L. and Leeper, F.J. (1998) J. Chem. Soc., Perkin Trans. 1, 1891-1894
65. Enders, D., Breuer, K., Kallfass, U., and Balensiefer, T. (2003) Synthesis, 1292-1295
66. Enders, D., Niemeier, O., and Balensiefer, T. (2006) Angew. Chem., Int. Ed., 45, 1463-1467
67. Kerr, M.S., de Alaniz, J.R., and Rovis, T. (2002) J. Am. Chem. Soc., 124, 10298-10299
68. Kerr, M.S. and Rovis, T. (2003) Synlett, 1934-1936
69. Kerr, M.S., de Alaniz, J.R., and Rovis, T. (2005) J. Org. Chem., 70, 5725-5728
70. Glorius, F., Altenhoff, A.G., Goddard, R., and Lehmann, C. (2002) Chem. Commun., 2704-2705
71. Herrmann, W.A., Goossen, L.J., Köcher, C., and Artus, G.R.J. (1996) Angew. Chem., Int. Ed., 35, 2805-2807
72. Baskakov, D., Herrmann, W.A., Herdtweck, E., and Hoffmann, S.D. (2007) Organometallics, 26, 626-632
73. Suzuki, Y., Yamauchi, K., Muramatsu, K., and Sato, M. (2004) Chem. Commun., 2770-2771
74. Li, G.-Q., Dai, L.-X., and You, S.-L. (2007) Chem. Commun., 852-854
75. Struble, J.R., Kaeobamrung, J., and Bode, J.W. (2008) Org. Lett., 10, 957-960
76. Takikawa, H. and Suzuki, K. (2007) Org. Lett., 9, 2713-2716.
77. Zhang, Y.-R., He, L., Wu, X., Shao, P.-L., and Ye, S. (2008) Org. Lett., 10, 277-280
78. He, L., Zhang, Y.-R., Huang, X.-L., and Ye, S. (2008) Synthesis, 2825-2829.
79. Gausepohl, R., Buskens, P., Kleinen, J., Bruckmann, A., Lehmann, C.W., Klankermayer, J., and Leitner, W. (2006) Angew. Chem., Int. Ed., 45, 3689-3692.
80. Myers, E.L., de Vries, J.G., and Aggarwal, V.K. (2007) Angew. Chem., Int. Ed., 46, 1893-1896.
81. Xu, Y.-M. and Shi, M. (2004) J. Org. Chem., 69, 417-425.
82. Juhl, K., Gathergood, N., and Jøgenson, A.K. (2001) Angew. Chem., Int. Ed., 40, 2995-2997.
83. Li, G., Kim, S.H., and Wei, H.-X. (2000) Tetrahedron, 56, 719-723.
84. Declerck, V., Martinez, J., and Lamaty, F. (2009) Chem. Rev., 109, 1-48.
85. Huang, J.-W. and Shi, M. (2003) Adv. Synth. Catal., 345, 953-958
86. Zhao, L.-J., Song He, H., Shi, M., and Toy, P.H. (2004) J. Comb. Chem., 6, 680-683
87. Zhao, L.-J., Kwong, C.K.-W., Shi, M., and Toy, P.H. (2005) Tetrahedron, 61, 12026-12032.
88. Shi, Y.-L., Xu, Y.-M., and Shi, M. (2004) Adv. Synth. Catal., 346, 1220-1230
89. Shi, Y.-L. and Shi, M. (2006) Tetrahedron, 62, 461-475
90. Back, T.G., Rankic, D.A., Sorbetti, J.M., and Wullf, J.E. (2005) Org. Lett., 7, 2377-2379.