Enantioselective allylation of N-(trimethylsilyl)benzaldehyde imine using polymer-supported chiral allylboron reagents

Polymer-supported chiral N-sulfonylamino alcohols 3 and 4 obtained from copolymerization of enantiomerically pure amino alcohols 1c and 2c derived from (1R)-(+)-camphor with styrene and divinylbenzene were treated with triallylborane, trimethallylborane, and tri(3,3-dimethylallyl)borane, respectively, to give polymeric allylating agents. N-(Trimethylsilyl)benzaldehyde imine was allowed to react with the polymeric chiral reagents to afford the corresponding primary homoallylamines in high yield and good enantioselectivities. (C) 1997 Elsevier Science Ltd.