Direct Asymmetric Organocatalytic Michael Reactions of α,α-Disubstituted Aldehydes with β-Nitrostyrenes for the Synthesis of Quaternary Carbon-Containing Products

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 α,α-dialkylaldehydes with (E)-β-nitrostyren...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2004-07, Vol.6 (15), p.2527-2530
Main Authors: Mase, Nobuyuki, Thayumanavan, Rajeswari, Tanaka, Fujie, Barbas, Carlos F
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Amines - chemistry
Carbon - chemistry
Catalysis
Molecular Structure
Proline - chemistry
Spectrometry, Fluorescence
Stereoisomerism
Styrenes - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 α,α-dialkylaldehydes with (E)-β-nitrostyrene provided the α,α-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049196o