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anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst.

Journal of the American Chemical Society (2005-11-25)
Taichi Kano, Yukako Yamaguchi, Osamu Tokuda, Keiji Maruoka
ABSTRACT

A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the alpha-imino ester 4 proceed smoothly to give the functional beta-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Isovaleraldehyde, 97%
Sigma-Aldrich
Isovaleraldehyde, ≥97%, FG
Sigma-Aldrich
Isovaleraldehyde, natural, ≥95%, FG