A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N‐Boc‐Protected Imines
Angewandte Chemie International EditionPublished 28 January 2009
Taichi Kano, Yukako Yamaguchi, Keiji Maruoka
Citations129
SJR quartileQ1
SJR score5.55
SNIP2.47
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TL;DR
The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes.
Abstract
Abstract The moderate nucleophilicity of the axially chiral amino sulfonamide ( S )‐ 1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N‐Boc‐protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc= tert ‐butoxycarbonyl, Tf=trifluoromethanesulfonyl). magnified image
Keywords
Chemistry
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