Efficient Cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13362-13363

  Degrado, Sylvia J ^a   Mizutani, Hirotake ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; KETONE; LIGAND; PEPTIDE; REAGENT; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CONJUGATION; REACTION ANALYSIS;

AMINO ACIDS; CATALYSIS; COPPER; DIPEPTIDES; HYDROCARBONS, CYCLIC; KETONES; ORGANOMETALLIC COMPOUNDS;

EID: 0037073198     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021081x     Document Type: Article

References (11)

1. Krause, N.; Hoffmann-Roder, A. Synthesis 2001, 171-196.
2. (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756.
3. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781.
4. (c) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
5. For catalytic asymmetric conjugate additions to trisubstituted α,β-unsaturated malonates (<60% ee), see: Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, F.; Benhaim, C. Synlett 2001, 1375-1378.
6. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 110, 388-401.
7. Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668-1671.
8. Equilibration reactions proceed to afford the less volatile products in 70 to >98% isolated yields.
9. See the Supporting Information for complete data regarding reactions in Table 2 when performed in the presence of 19 (except entries 9 and 10).
10. See the Supporting Information for experimental details.
11. Choi, H. Y.; Choi, J. Y.; Yang, H. Y.; Kim, Y. H. Tetrahedron: Asymmetry 2002, 13, 801-804.