Remote asymmetric induction in reactions between 4- and 5-benzyloxypent-2-enyl(tributyl)stannanes and chiral imines prepared from butyl glyoxylate

Abstract

Transmetallation of 4- and 5-benzyloxypent-2-enyl(tributyl)stannanes 13 and 18 with tin(IV) chloride generates intermediate allyltin trichlorides which react with imines 9 and ent-9, prepared from butyl glyoxylate and either (R)- or (S)-1-phenylethylamine, with effective 1,5-asymmetric induction.