Control and applications of remote asymmetric induction using allylmetal reagents

Abstract

Treatment of hydroxy- and alkoxy-substituted allylstannanes with tin(IV) halides effects transmetallation and the stereoselective formation of allyltin trihalides. These react with aldehydes and imines derived from glyoxylates with useful levels of remote asymmetric induction. Aspects of this chemistry are discussed, together with the conversion of the products into tetrahydrofurans and dihydropyrans.