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Direct asymmetric organocatalytic Michael reactions of alpha,alpha-disubstituted aldehydes with beta-nitrostyrenes for the synthesis of quaternary carbon-containing products.
Org Lett. 2004 Jul 22; 6(15):2527-30.OL

Abstract

[reaction: see text] Direct asymmetric catalytic Michael reactions have been performed using chiral-amine/acid bifunctional catalysts. Performed with 0.3 equiv of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and 0.3 equiv of trifluoroacetic acid as the catalyst, the reaction of alpha,alpha-dialkylaldehydes with (E)-beta-nitrostyrene provided the alpha,alpha-dialkyl Michael products in up to 96% yield with up to 91% ee. With respect to enantioselectivity, l-proline was a poor catalyst of this class of Michael reactions.

Authors+Show Affiliations

Mase N
The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Thayumanavan R
No affiliation info available
Tanaka F
No affiliation info available
Barbas CF
No affiliation info available

MeSH

AldehydesAminesCarbonCatalysisMolecular StructureProlineSpectrometry, FluorescenceStereoisomerismStyrenes

Pub Type(s)

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

Language

eng

PubMed ID

15255682

Citation

Mase, Nobuyuki, et al. "Direct Asymmetric Organocatalytic Michael Reactions of Alpha,alpha-disubstituted Aldehydes With Beta-nitrostyrenes for the Synthesis of Quaternary Carbon-containing Products." Organic Letters, vol. 6, no. 15, 2004, pp. 2527-30.
Mase N, Thayumanavan R, Tanaka F, et al. Direct asymmetric organocatalytic Michael reactions of alpha,alpha-disubstituted aldehydes with beta-nitrostyrenes for the synthesis of quaternary carbon-containing products. Org Lett. 2004;6(15):2527-30.
Mase, N., Thayumanavan, R., Tanaka, F., & Barbas, C. F. (2004). Direct asymmetric organocatalytic Michael reactions of alpha,alpha-disubstituted aldehydes with beta-nitrostyrenes for the synthesis of quaternary carbon-containing products. Organic Letters, 6(15), 2527-30.
Mase N, et al. Direct Asymmetric Organocatalytic Michael Reactions of Alpha,alpha-disubstituted Aldehydes With Beta-nitrostyrenes for the Synthesis of Quaternary Carbon-containing Products. Org Lett. 2004 Jul 22;6(15):2527-30. PubMed PMID: 15255682.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric organocatalytic Michael reactions of alpha,alpha-disubstituted aldehydes with beta-nitrostyrenes for the synthesis of quaternary carbon-containing products. AU - Mase,Nobuyuki, AU - Thayumanavan,Rajeswari, AU - Tanaka,Fujie, AU - Barbas,Carlos F,3rd PY - 2004/7/17/pubmed PY - 2005/2/11/medline PY - 2004/7/17/entrez SP - 2527 EP - 30 JF - Organic letters JO - Org Lett VL - 6 IS - 15 N2 - [reaction: see text] Direct asymmetric catalytic Michael reactions have been performed using chiral-amine/acid bifunctional catalysts. Performed with 0.3 equiv of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and 0.3 equiv of trifluoroacetic acid as the catalyst, the reaction of alpha,alpha-dialkylaldehydes with (E)-beta-nitrostyrene provided the alpha,alpha-dialkyl Michael products in up to 96% yield with up to 91% ee. With respect to enantioselectivity, l-proline was a poor catalyst of this class of Michael reactions. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15255682/Direct_asymmetric_organocatalytic_Michael_reactions_of_alphaalpha_disubstituted_aldehydes_with_beta_nitrostyrenes_for_the_synthesis_of_quaternary_carbon_containing_products_ DB - PRIME DP - Unbound Medicine ER -