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Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids.
J Am Chem Soc. 2005 Aug 17; 127(32):11256-7.JA

Abstract

Cinchona alkaloids catalyze the enantioselective Mannich reaction of beta-keto esters with acyl aryl imines. The reaction requires 10 mol % of cinchonine or cinchonidine. The reaction products are obtained in good yields (81-99%), high enantioselectivities (80-96% ee), and in diastereoselectivities that range from 1:1 to >95:5. The cinchonine-catalyzed reaction provides access to highly functionalized building blocks used in the asymmetric synthesis of a dihydropyrimidone and beta-amino alcohol.

Authors+Show Affiliations

Lou S
Department of Chemistry and Center for Chemical Methodology and Library Development, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, USA.
Taoka BM
No affiliation info available
Ting A
No affiliation info available
Schaus SE
No affiliation info available

MeSH

CatalysisCinchona AlkaloidsEstersIminesKetonesMannich Bases

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

16089450

Citation

Lou, Sha, et al. "Asymmetric Mannich Reactions of Beta-keto Esters With Acyl Imines Catalyzed By Cinchona Alkaloids." Journal of the American Chemical Society, vol. 127, no. 32, 2005, pp. 11256-7.
Lou S, Taoka BM, Ting A, et al. Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. J Am Chem Soc. 2005;127(32):11256-7.
Lou, S., Taoka, B. M., Ting, A., & Schaus, S. E. (2005). Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. Journal of the American Chemical Society, 127(32), 11256-7.
Lou S, et al. Asymmetric Mannich Reactions of Beta-keto Esters With Acyl Imines Catalyzed By Cinchona Alkaloids. J Am Chem Soc. 2005 Aug 17;127(32):11256-7. PubMed PMID: 16089450.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. AU - Lou,Sha, AU - Taoka,Brandon M, AU - Ting,Amal, AU - Schaus,Scott E, PY - 2005/8/11/pubmed PY - 2005/12/13/medline PY - 2005/8/11/entrez SP - 11256 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 32 N2 - Cinchona alkaloids catalyze the enantioselective Mannich reaction of beta-keto esters with acyl aryl imines. The reaction requires 10 mol % of cinchonine or cinchonidine. The reaction products are obtained in good yields (81-99%), high enantioselectivities (80-96% ee), and in diastereoselectivities that range from 1:1 to >95:5. The cinchonine-catalyzed reaction provides access to highly functionalized building blocks used in the asymmetric synthesis of a dihydropyrimidone and beta-amino alcohol. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16089450/Asymmetric_Mannich_reactions_of_beta_keto_esters_with_acyl_imines_catalyzed_by_cinchona_alkaloids_ DB - PRIME DP - Unbound Medicine ER -