Organic letters

Enantioselective recognition of 1, 2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds

KM Kim, H Park, HJ Kim, J Chin, W Nam

Index: Kwan, Mook Kim; Park, Hyunjung; Kim, Hae-Jo; Chin, Jik; Nam, Wonwoo Organic Letters, 2005 , vol. 7, # 16 p. 3525 - 3527

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Citation Number: 47

Abstract

A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1, 2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition.