Extending the Scope of the Evans Asymmetric Aldol Reaction: Preparation of Anti and “Non-Evans” Syn Aldols

Journal of Organic Chemistry

Volumn 56, Issue 20, 1991, Pages 5747-5750

  Walker, Michael A ^a   Heathcock, Clayton H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342713705     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00020a006     Document Type: Article

References (50)

1. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499.
2. Heathcock, C. H. Science 1981, 214, 396.
3. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
4. Mukaiyama, T. Organic Reactions; Wiley: New York, 1982; VoL 28.
5. Heathcock, C. H. In Comprehensive Carbanion Chemistry, Buncel E., Durst, T., Eds.; Elsevier: Amsterdam, 1984.
6. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2.
7. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
8. Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24.
9. Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278.
10. Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897.
11. Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441.
12. Evans, D. A.; Clark, S. J.; Rainer, M.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866.
13. Heathcock, C. H. Aldrichimica Acta 1990, 23, 99.
14. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976.
15. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
16. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
17. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
18. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
19. Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489.
20. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499.
21. Danda, H.; Hansen, M. N.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173.
22. Mulzer, J.; Brüntrup, G.; Finke, J.; Zippel, M. J. Am. Chem. Soc. 1979, 101, 7723.
23. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
24. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413.
25. Dougherty, D. Tetahedron Lett. 1982, 23, 4891.
26. Denmark, S. E.; Weber, E. J. Hel V. Chim. Acta 1983, 66, 1655.
27. Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1065.
28. Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970.
29. Dubois, J.-E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1984, 25, 4655.
30. Reetz, M. T.; Kesseler, K.; Jung, A. Tetahedron 1984, 40, 4327.
31. Reetz, M. T.; Sauerwald, M. J. Org. Chem. 1984, 50, 2292.
32. Heathcock, C. H.; Davidsen, S. K.; Hug, K. T.; Flippin, L. A. J. Org. Chem. 1986, 51, 3027.
33. Anh, N. T.; Thanh, B. T. Nouv. J. Chim. 1986, 10, 681.
34. Gennari, C.; Bereite, M. G.; Bernardi, A.; Moro, G.; Scolastico, C.; Todeschini, R. Tetrahedron 1986, 42, 893.
35. Brook, M. A.; Seebach, D. Can. J. Chem. 1987, 65, 836.
36. Denmark, S. E.; Henke, B. R.; Weber, E. J. Am. Chem. Soc. 1987, 109, 2512.
37. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.
38. Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481.
39. Nakamura, E.; Yamago, S.; McHii, D.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 2207.
40. Gennari, C. In Stereoselectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed.; Kluwer Academic Publishers: Dordechet, 1989; Chapter 4.
41. Oare, D.; Heathcock, C. H. Topics in Stereochemistry, Eliel, E. L., Wilen, S. H., Eds.; John Wiley and Sons: New York, 1991; Vol. 20, pp 161-165.
42. Satchell, D. P. N.; Satchell, R. S. Chem. Rev. 1969, 69, 251.
43. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256.
44. Lazio, P.; Teeton, M. J. Am. Chem. Soc. 1990, 112, 8750.
45. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Hiedelberg, 1986.
46. Denmark, S. E.; Henke, B. R.; Weber, E. J. Am. Chem. Soc. 1987, 109, 2512.
47. Kiyooka, S.; Nakano, M.; Shiota, F.; Fujiyama, R. J. Org. Chem. 1989, 54, 5409.
48. Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 77, 83.
49. Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Angew. Chem., Int. Ed. Engl. 1987, 26, 1184.
50. Pridgen, L. N.; Prol, Jr., J.; Alexander, B.; Gillyard, L. j. Org. Chem. 1989, 54, 3231.