Catalytic enantioselective allylation with chiral Lewis bases

Chemical Communications

Volumn , Issue 2, 2003, Pages 167-170

  Denmark, Scott E ^a   Fu, Jiping ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYL ALCOHOL; BASE; LEWIS BASE; SEROTONIN ANTAGONIST; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STOICHIOMETRY;

EID: 0037251137     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208065f     Document Type: Article

References (43)

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24. (a) S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2001, 123, 9488; (b) The large scale preparation of R-(l,l)- and S-(l,l)-2,2′-bispyrrolidine was easily accomplished on by photodimerization of pyrrolidine followed by resolution with tartaric acid. Org. Syn. manuscript submitted.
25. (a) S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2001, 123, 9488; (b) The large scale preparation of R-(l,l)- and S-(l,l)-2,2′-bispyrrolidine was easily accomplished on by photodimerization of pyrrolidine followed by resolution with tartaric acid. Org. Syn. manuscript submitted.
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39. For Lewis bases catalyzed aldol reactions: (a) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432. Epoxide opening reactions (b) S. E. Denmark, P. A. Barsanti, K.-T. Wong and R. A. Stavenger, J. Org. Chem., 1998, 63, 2428; (c) S. E. Denmark, T. Wynn and B. G. Jellerichs, Angew. Chem., Int. Ed., 2001, 40, 2255. Reactions promoted by silicon tetrachloride (d) S. E. Denmark and T. Wynn, J. Am. Chem. Soc., 2001, 123, 6199; (e) S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.
40. For Lewis bases catalyzed aldol reactions: (a) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432. Epoxide opening reactions (b) S. E. Denmark, P. A. Barsanti, K.-T. Wong and R. A. Stavenger, J. Org. Chem., 1998, 63, 2428; (c) S. E. Denmark, T. Wynn and B. G. Jellerichs, Angew. Chem., Int. Ed., 2001, 40, 2255. Reactions promoted by silicon tetrachloride (d) S. E. Denmark and T. Wynn, J. Am. Chem. Soc., 2001, 123, 6199; (e) S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.
41. For Lewis bases catalyzed aldol reactions: (a) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432. Epoxide opening reactions (b) S. E. Denmark, P. A. Barsanti, K.-T. Wong and R. A. Stavenger, J. Org. Chem., 1998, 63, 2428; (c) S. E. Denmark, T. Wynn and B. G. Jellerichs, Angew. Chem., Int. Ed., 2001, 40, 2255. Reactions promoted by silicon tetrachloride (d) S. E. Denmark and T. Wynn, J. Am. Chem. Soc., 2001, 123, 6199; (e) S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.
42. For Lewis bases catalyzed aldol reactions: (a) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432. Epoxide opening reactions (b) S. E. Denmark, P. A. Barsanti, K.-T. Wong and R. A. Stavenger, J. Org. Chem., 1998, 63, 2428; (c) S. E. Denmark, T. Wynn and B. G. Jellerichs, Angew. Chem., Int. Ed., 2001, 40, 2255. Reactions promoted by silicon tetrachloride (d) S. E. Denmark and T. Wynn, J. Am. Chem. Soc., 2001, 123, 6199; (e) S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.
43. For Lewis bases catalyzed aldol reactions: (a) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2000, 33, 432. Epoxide opening reactions (b) S. E. Denmark, P. A. Barsanti, K.-T. Wong and R. A. Stavenger, J. Org. Chem., 1998, 63, 2428; (c) S. E. Denmark, T. Wynn and B. G. Jellerichs, Angew. Chem., Int. Ed., 2001, 40, 2255. Reactions promoted by silicon tetrachloride (d) S. E. Denmark and T. Wynn, J. Am. Chem. Soc., 2001, 123, 6199; (e) S. E. Denmark, T. Wynn and G. L. Beutner, J. Am. Chem. Soc., 2002, 124, 13405.