Diastereoselectivity in asymmetric allylations: The role of vicinal chirality in the allyl nucleophile for SE2′ reactions with aldehydes

Canadian Journal of Chemistry

Volumn 82, Issue 2, 2004, Pages 120-130

  Williams, David R ^a   Meyer, Kevin G ^a   Shamim, Khalida ^a   Patnaik, Samarjit ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

1,4 stereocontrol; Asymmetric allylation; Diastereofacial selectivity; Homoallylic alcohols

Indexed keywords

ALDEHYDES; IN SITU PROCESSING; MATHEMATICAL MODELS; STEREOCHEMISTRY; SULFUR COMPOUNDS;

ALLYL MOIETY; ALLYLATION; LIGANDS; NUCLEOPHILES;

ALCOHOLS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLYL COMPOUND; SULFONAMIDE;

ALDOL REACTION; ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DIASTEREOISOMER; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 2342530383     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-168     Document Type: Article

References (31)

1. For a general review: Y. Yamamoto and N. Asao. Chem. Rev. 93, 2207 (1993).
2. (a) W.R. Roush. Comprehensive organic synthesis. Vol. 2. Edited by B.A. Trost and I. Fleming. Pergamon Press, Oxford. 1991;
3. (b) P.V. Ramachandran. Aldrichimica Acta, 35, 23 (2002).
4. S.R. Chemler and W.R. Roush. Recent applications of the allylation reaction to the synthesis of natural products. In Modern carbonyl chemistry. Edited by J. Otera. Wiley-VCH, Weinheim, Germany. 2000.
5. E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989).
6. E.J. Corey, C.-M. Yu, and D.-H. Lee. J. Am. Chem. Soc. 112, 878 (1990).
7. D.R. Williams, D.A. Brooks, and M.A. Berliner. J. Am. Chem. Soc. 121, 4924 (1999).
8. D.R. Williams and K.G. Meyer. J. Am. Chem. Soc. 123, 765 (2001).
9. D.R. Williams, A.A. Kiryanov, U. Emde, M.P. Clark, M.A. Berliner, and J.T. Reeves. Angew. Chem. Int. Ed. 42, 1258 (2003).
10. D.R. Williams, D.A. Brooks, K.G. Meyer, and M.P. Clark. Tetrahedron Lett. 39, 7251 (1998).
11. Y. Nishigaichi, H. Kuramoto, and A. Takuwa. Tetrahedron Lett. 36, 3353 (1995).
12. R.J. Maguire, J. Mulzer, and J.W. Bats. J. Org. Chem. 61, 6936 (1996);
13. (b) R.J. Maguire, J. Mulzer, and J.W. Bats. Tetrahedron Lett. 37, 5487 (1996).
14. D.R. Williams, W.S. Kissel, and J.J. Li. Tetrahedron Lett. 39, 8593 (1998).
15. B.M. Trost, T.A. Grese, and D.M.T. Chan. J. Am. Chem. Soc. 113, 7350 (1991).
16. E. Piers, J.M. Chong, K. Gustafson, and R.J. Andersen. Can. J. Chem. 62, 1 (1984).
17. Sharpless asymmetric epoxidations proceeded with >97% de; see: Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless. J. Am. Chem. Soc. 109, 5765 (1987).
18. S.D. Burke, J.L. Buchanan, and J.D. Rovin. Tetrahedron Lett. 32, 3961 (1991).
19. B.M. Trost and S.A. King. J. Am. Chem. Soc. 112, 408 (1990).
20. (a) I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa. J. Am. Chem. Soc. 113, 4092 (1991);
21. (b) J.A. Dale and H.S. Mosher. J. Am. Chem. Soc. 95, 512 (1973).
22. D.A. Evans, M.J. Dart, J.L. Duffy, and M.G. Yang. J. Am. Chem. Soc. 118, 4322 (1996).
23. For a related discussion: W.R. Roush and L. Banfi. J. Am. Chem. Soc. 110, 3979 (1988).
24. R. W. Hoffmann. Chem. Rev. 89, 1841 (1989).
25. For a leading reference: J. Haller, T. Strassner, and K.M. Houk. J. Am. Chem. Soc. 119, 8031 (1997).
26. (a) D.A. Evans, H.P. Ng, J.S. Clark, and D.L. Rieger. Tetrahedron, 48, 2127 (1992);
27. (b) I. Paterson. Pure Appl. Chem. 64, 1821 (1992);
28. (c) D.A. Evans and M.A. Calter. Tetrahedron Lett. 34, 6871 (1993);
29. (d) I. Paterson, D.J. Wallace, and S.M. Velázquez. Tetrahedron Lett. 35, 9083 (1994).
30. D.R. Williams, S.V. Plummer, and S. Patnaik. Angew. Chem. Int Ed. 42, 3934 (2003).
31. D. R. Williams, M. P. Clark, U. Emde, and M. A. Berliner. Org. Lett. 2, 3023 (2000).