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A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-Protected Imines

✍ Scribed by Taichi Kano; Yukako Yamaguchi; Keiji Maruoka

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
266 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis

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

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