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anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst

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Taichi Kano, Yukako Yamaguchi, Osamu Tokuda, and Keiji Maruoka*

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

J. Am. Chem. Soc., 2005, 127 (47), pp 16408–16409

DOI: 10.1021/ja056008w

Publication Date (Web): November 2, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, maruoka@kuchem.kyoto-u.ac.jp

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 α-imino ester 4 proceed smoothly to give the functional β-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible.

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Published In Issue November 30, 2005
Received September 1, 2005

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Communication

anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst

Abstract

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History

Recommend & Share

Related Content

Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid

Direct Catalytic Asymmetric Synthesis of anti-1,2-Amino Alcohols and syn-1,2-Diols through Organocatalytic anti-Mannich and syn-Aldol Reactions

Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes

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