Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates

Chemical Communications

Volumn 48, Issue 42, 2012, Pages 5076-5078

  Okamura, Takaaki ^a   Asano, Keisuke ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBOXYL GROUP; CINCHONA ALKALOID; HYDROXYL GROUP; THIOESTER;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION ANALYSIS;

EID: 84860360934     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc31602a     Document Type: Article

References (59)

1. M. Misra, R. Luthra, K. L. Singh and K. Sushil, in Comprehensive Natural Products Chemistry, ed. S. D. Barton, K. Nakanishi and O. Meth-Cohn, Pergamon, Oxford, UK, 1999, vol. 4
2. For reviews, see: Modern Aldol Reactions, ed. R. Mahrwald, Wiley-VCH, Weinheim, 2004
3. B. Alcaide, P. Almendros, Eur. J. Org. Chem., 2002, 1595
4. B. Schetter, R. Mahrwald, Angew. Chem., Int. Ed., 2006, 45, 7506
5. B. M. Trost, C. S. Brindle, Chem. Soc. Rev., 2010, 39, 1600
6. R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc., 1987, 109, 5856
7. D. J. Ager, S. A. Laneman, Tetrahedron: Asymmetry, 1997, 8, 3327
8. R. Noyori, Angew. Chem., Int. Ed., 2002, 41, 2008
9. C. F. Nising, S. Bräse, Chem. Soc. Rev., 2008, 37, 1218
10. E. Hartmann, D. J. Vyas, M. Oestreich, Chem. Commun., 2011, 47, 7917
11. C. F. Nising, S. Bräse, Chem. Soc. Rev., 2012, 41, 988
12. A. J. Boersma, D. Coquière, D. Geerdink, F. Rosati, B. L. Feringa, G. Roelfes, Nat. Chem., 2010, 2, 991
13. D. A. Evans, J. A. Gauchet-Prunet, J. Org. Chem., 1993, 58, 2446
14. H. Watanabe, K. Machida, D. Itoh, H. Nagatsuka, T. Kitahara, Chirality, 2001, 13, 379
15. P. A. Evans, A. Grisin, M. J. Lawler, J. Am. Chem. Soc., 2012, 134, 2856
16. D. Yoo, J. S. Oh, Y. G. Kim, Org. Lett., 2002, 4, 1213
17. D. Yoo, S. Kwon, Y. G. Kim, Tetrahedron: Asymmetry, 2005, 16, 3762
18. H. Kim, D. Yoo, S. Kwon, Y. G. Kim, Tetrahedron: Asymmetry, 2009, 20, 2715
19. S. Cardani, C. Gennari, C. Scolastico, R. Villa, Tetrahedron, 1989, 45, 7397
20. A. Bernardi, S. Cardani, C. Scolastico, R. Villa, Tetrahedron, 1990, 46, 1987
21. S. Cardani, C. Scolastico, R. Villa, Tetrahedron, 1990, 46, 7283
22. F.-A. Kang, Z.-Q. Yu, H.-Y. Yin, C.-L. Yin, Tetrahedron: Asymmetry, 1997, 8, 3591
23. J. Mulzer, M. Kappert, G. Huttner, I. Jibril, Angew. Chem., Int. Ed. Engl., 1984, 23, 704
24. A. Dondoni, P. Merino, J. Orduna, Tetrahedron Lett., 1991, 32, 3247
25. A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc., 1994, 116, 3324
26. C. Fehr, O. Guntern, Helv. Chim. Acta, 1992, 75, 1023
27. C. Fehr, J. Galindo, Helv. Chim. Acta, 2005, 88, 3128
28. D. J. Buchanan, D. J. Dixon, F. A. Hernandez-Juan, Org. Lett., 2004, 6, 1357
29. F. A. Hernandez-Juan, X. Xiong, S. E. Brewer, D. J. Buchanan, D. J. Dixon, Synthesis, 2005, 3283
30. F. A. Hernandez-Juan, R. D. Richardson, D. J. Dixon, Synlett, 2006, 2673
31. X. Xiong, C. Ovens, A. W. Pilling, J. W. Ward, D. J. Dixon, Org. Lett., 2008, 10, 565
32. Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc., 2006, 128, 9328
33. D. B. Ramachary, R. Mondal, Tetrahedron Lett., 2006, 47, 7689
34. T. Kano, Y. Tanaka, K. Maruoka, Tetrahedron, 2007, 63, 8658
35. C. D. Vanderwal, E. N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 14724
36. S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc., 2007, 129, 1536
37. A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Eur. J. Org. Chem., 2007, 5492
38. C. M. Reisinger, X. Wang, B. List, Angew. Chem., Int. Ed., 2008, 47, 8112
39. D. R. Li, A. Murugan, J. R. Falck, J. Am. Chem. Soc., 2008, 130, 46
40. T.-L. Ho, Tactics of Organic Synthesis, Wiley, New York, 1994
41. N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem., Int. Ed., 2009, 48, 2854
42. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem., Int. Ed. Engl., 1985, 24, 1
43. M. Braun, Angew. Chem., Int. Ed. Engl., 1987, 26, 24
44. K. Asano, S. Matsubara, Org. Lett., 2012, 14, 1620
45. K. Asano, S. Matsubara, J. Am. Chem. Soc., 2011, 133, 16711
46. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672
47. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc., 2005, 127, 119
48. B. Vakulya, S. Varga, A. Csámpai, T. Soós, Org. Lett., 2005, 7, 1967
49. A. Hamza, G. Schubert, T. Soós, I. Pápai, J. Am. Chem. Soc., 2006, 128, 13151
50. S. J. Connon, Chem.-Eur. J., 2006, 12, 5418
51. R. I. Hollingsworth, G. Wang, Chem. Rev., 2000, 100, 4267
52. G. Wang, R. I. Hollingsworth, J. Org. Chem., 1999, 64, 1036
53. G. Wang, R. I. Hollingsworth, Tetrahedron: Asymmetry, 2000, 11, 4429
54. H. Yang, N. Goyal, J. R. Ella-Menye, K. Williams, G. Wang, Synthesis, 2012, 561
55. H. C. Kolb, Y. L. Bennani, K. B. Sharpless, Tetrahedron: Asymmetry, 1993, 4, 133
56. A. Alexakis, P. Mangeney, Tetrahedron: Asymmetry, 1990, 1, 477
57. Classics in Stereoselective Synthesis, ed. E. M. Carreira and L. Kvaerno, Wiley-VCH, Weinheim, 2009, ch. 6
58. L. S. Liebeskind, J. Srogl, J. Am. Chem. Soc., 2000, 122, 11260
59. Y. Yu, L. S. Liebeskind, J. Org. Chem., 2004, 69, 3554