ASYMMETRIC SYNTHESIS VIA CHIRAL SILICON REAGENTS. CHIRAL α-HYDROXYALKYL ANION EQUIVALENTS FROM VINYLSILANES CONTAINING OPTICALLY ACTIVE AMINO OR ALKOXY GROUPS ON SILICON

Article abstract of DOI:10.1016/S0040-4039(01)90074-7

Chiral vinylsilanes containing optically active functional groups on silicon have been used as precursors for chiral α-hydroxyalkyl anion equivalents via a sequence of addition of n-butyllithium, coupling with organic halides, and oxidative cleavage of the silicon-carbon bond, to give optically active alcohols of up to 60percent ee.