Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates

Angewandte Chemie - International Edition

Volumn 50, Issue 28, 2011, Pages 6392-6395

  Xu, Xinfang ^a   Hu, Wen Hao ^b   Doyle, Michael P ^a  

^a University of Maryland   (United States)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

1,5 diesters; asymmetric catalysis; copper; Mukaiyama Michael addition; synthetic methods

Indexed keywords

1,5-DIESTERS; ASYMMETRIC CATALYSIS; CATALYTIC SYNTHESIS; COPPER (II); EFFICIENT METHOD; ENANTIOSELECTIVE; FUNCTIONALIZED; LEWIS ACID; MUKAIYAMA-MICHAEL ADDITION; SYNTHETIC METHODS; TERT-BUTYLDIMETHYLSILYL;

ADDITION REACTIONS;

ACETOACETIC ACID DERIVATIVE; AZO COMPOUND; COPPER; LEWIS ACID;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETOACETATES; AZO COMPOUNDS; CATALYSIS; COPPER; LEWIS ACIDS; STEREOISOMERISM;

EID: 79959910065     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102405     Document Type: Article

References (88)

1. For comprehensive reviews, see
2. R. Little, M. Masjedizadeh, O. Wallquist, J. Mcloughlin, Org. React. 1995, 47, 315
3. K. Tomioka, Y. Nagaoka, in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Heidelberg, 1999, chap. 29.1
4. M. Kanai, M. Shibasaki, in Catalytic Asymmetric Synthesis, 2 nd ed., (Ed.: I. Ojima,), Wiley, New York, 2000, p. 569
5. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346
6. J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726
7. Angew. Chem. Int. Ed. 2003, 42, 1688
8. E. Wang, J. Wang, H. Ji, Angew. Chem. 2005, 117, 1393
9. Angew. Chem. Int. Ed. 2005, 44, 1369
10. I. D. Gridnev, M. Watanabe, H. Wang, T. Ikariya, J. Am. Chem. Soc. 2010, 132, 16637
11. D. A. Evans, S. Mito, D. Seidel, J. Am. Chem. Soc. 2007, 129, 11583
12. S. Jautze, R. Peters, Synthesis 2010, 365
13. S. Boncel, A. Gondela, K. Walczak, Synthesis 2010, 1573
14. V. A. Soloshonok, H. Ueki, T. K. Ellis, ACS Symp. Ser. 2009, 1009, 72
15. H. Yang, S. Kim, Synlett 2008, 555
16. U. Kazmaier, Angew. Chem. 2009, 121, 5902
17. Angew. Chem. Int. Ed. 2009, 48, 5790
18. D. Enders, C. Wang, J. X. Liebich, Chem. Eur. J. 2009, 15, 11058
19. W. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 3095
20. P. R. Krishna, A. Sreeshailam, R. Srinivas, Tetrahedron 2009, 65, 9657
21. M. Santanu, J.-W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
22. P. Melchiorre, K. A. Jørgensen, J. Org. Chem. 2003, 68, 4151.
23. For reviews of the Mukaiyama-Michael reaction, see
24. S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 102, 2227
25. A. Takahashi, H. Yanai, M. Zhang, T. Sonoda, M. Mishima, T. Taguchi, J. Org. Chem. 2010, 75, 1259; selected recent examples
26. C. J. Borths, D. E. Carrera, D. W. C. MacMillan, Tetrahedron 2009, 65, 6746
27. H. Tamagaki, Y. Nawate, R. Nagase, Y. Tanabe, Chem. Commun. 2010, 46, 5930
28. M. O. Ratnikov, V. V. Tumanov, W. A. Smit, Angew. Chem. 2008, 120, 9885
29. Angew. Chem. Int. Ed. 2008, 47, 9739.
30. Examples of Lewis acid catalyzed asymmetric reactions, see
31. D. A. Evans, T. Rovis, M. C. Kozlowski, J. S. Tedrow, J. Am. Chem. Soc. 1999, 121, 1994
32. D. A. Evans, M. C. Willis, J. N. Johnston, Org. Lett. 1999, 1, 865
33. D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635
34. D. A. Evans, T. Rovis, M. C. Kozlowski, C. W. Downey, J. S. Tedrow, J. Am. Chem. Soc. 2000, 122, 9134
35. D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480
36. T. Harada, H. Iwai, H. Takatsuki, K. Fujita, M. Kubo, A. Oku, Org. Lett. 2001, 3, 2101
37. H. Suga, T. Kitamura, A. Kakehi, T. Baba, Chem. Commun. 2004, 1414
38. T. Harada, S. Adachi, X. Wang, Org. Lett. 2004, 6, 4877
39. G. Desimoni, G. Faita, M. Guala, A. Laurenti, M. Mella, Chem. Eur. J. 2005, 11, 3816
40. K. Ishihara, M. Fushimi, Org. Lett. 2006, 8, 1921
41. N. Takenaka, J. Abell, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 742
42. W. Zheng, Z. Zhang, M. J. Kaplan, J. C. Antilla, J. Am. Chem. Soc. 2011, 133, 3339
43. B. M. Trost, J. Hitce, J. Am. Chem. Soc. 2009, 131, 4572
44. T. Gendrineau, O. Chuzel, H. Eijsberg, J. P. Genet, S. Darses, Angew. Chem. 2008, 120, 7783
45. Angew. Chem. Int. Ed. 2008, 47, 7669
46. D. A. Evans, R. J. Thomson, F. Franco, J. Am. Chem. Soc. 2005, 127, 10816
47. G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 4442
48. C. Mazet, E. N. Jacobsen, Angew. Chem. 2008, 120, 1786
49. Angew. Chem. Int. Ed. 2008, 47, 1762
50. N. Madhavana, M. Weck, Adv. Synth. Catal. 2008, 350, 419.
51. For examples of organocatalytic asymmetric reactions, see
52. F. Zhang, E. J. Corey, Org. Lett. 2001, 3, 639
53. S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192
54. Y. Zhu, J. P. Malerich, V. H. Rawal, Angew. Chem. 2010, 122, 157
55. Angew. Chem. Int. Ed. 2010, 49, 153
56. S.-L. Zhu, S.-Y. Yu, D.-W. Ma, Angew. Chem. 2008, 120, 555
57. Angew. Chem. Int. Ed. 2008, 47, 545
58. H. C. Huang, Z.-C. Jin, K.-L. Zhu, X.-M. Liang, J.-X. Ye, Angew. Chem. 2011, 123, 3290
59. Angew. Chem. Int. Ed. 2011, 50, 3232
60. D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin, A. D. Smith, J. Am. Chem. Soc. 2011, 133, 2714
61. S. Mukherjee, J.-W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
62. M. P. Doyle, K. Kundu, A. E. Russell, Org. Lett. 2005, 7, 5171.
63. L. Yu, Y. Zhang, N. Jee, M. P. Doyle, Org. Lett. 2008, 10, 1605.
64. L. Yu, K. Bakshi, P. Zavalij, M. P. Doyle, Org. Lett. 2010, 12, 4304
65. L. Zhou, M. P. Doyle, Org. Lett. 2010, 12, 796.
66. K. Kundu, M. P. Doyle, Tetrahedron: Asymmetry 2006, 17, 574.
67. J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325
68. D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238.
69. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. S. Xu, J. Am. Chem. Soc. 2007, 129, 10029
70. D. A. Evans, H.-J. Song, K. R. Fandrick, Org. Lett. 2006, 8, 3351
71. X.-Y. Guan, L.-P. Yang, W.-H. Hu, Angew. Chem. 2010, 122, 2236
72. Angew. Chem. Int. Ed. 2010, 49, 2190
73. B. M. Trost, K. Lehr, D. J. Michaelis, J. Xu, A. K. Buckl, J. Am. Chem. Soc. 2010, 132, 8915
74. M. C. Myers, A. R. Bharadwaj, B. C. Milgram, K. A. Scheidt, J. Am. Chem. Soc. 2005, 127, 14675
75. A. J. Boersma, B. L. Feringa, G. Roelfes, Org. Lett. 2007, 9, 3647.
76. D. A. Evans, C. E. Masse, J. Wu, Org. Lett. 2002, 4, 3375
77. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236.
78. 6 (2.0 equiv) according to:, D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669; and Ref. [3e].
79. A. Hasegawa, F. Ono, S. Kanemasa, Tetrahedron Lett. 2008, 49, 5220
80. F. Ono, M. Hasegawa, S. Kanemasa, J. Tanaka, Tetrahedron Lett. 2008, 49, 5105.
81. For the 1S,3S and 1S,3R isomers, see
82. P. D. Theisen, C. H. Heathcock, J. Org. Chem. 1993, 58, 142; for the 1R,3S and 1R,3R isomers, see
83. R. Verma, S. Mithran, S. K. Ghosh, J. Chem. Soc. Perkin Trans. 1 1999, 257.
84. M. Regitz, G. Maas, Diazo Compounds 2 Properties and Sythesis (Eds.:, M. Regitz, G. Maas,), Academic Press, Inc., Orlando, 1986
85. M. P. Doyle, M. A. McKervey, T. Ye, in Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998
86. M. P. Doyle, A. J. Catino, Tetrahedron: Asymmetry 2003, 14, 925
87. M. P. Doyle, Y.-H. Wang, P. Ghorbani, E. Bappert, Org. Lett. 2005, 7, 5035.
88. See Ref. [10b] and Ref. [10c].