Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives

Optically pure 1,3,2-oxazasilolidine derivatives were synthesized from a chiral 1,2-amino alcohol. These heterocyclic compounds containing a stereogenic silicon atom produced tertiary silanes with excellent optical purity through successive reactions with Grignard reagents and diisobutylaluminum hydride. Stereochemical course of the reactions of the oxazasilolidine at the chiral silicon atom was elucidated based on the absolute configurations of the products and the substrate which were determined by chiral HPLC and X-ray crystallographic analyses. (C) 2009 Elsevier B. V. All rights reserved.