Abstract
(R)- and (S)-[(benzyloxy)methyl](tert-butyl)methylsilane [(−)-(R)-1 and (+)-(S)-1], possessing a stereogenic center at the Si-atom, were prepared in highly enantiomerically enriched form by resolution via diastereomeric silyl ethers. Conversion of the hydrosilanes into different functionalized chiral silanes by direct or stepwise substitution of the (Si)–H-atom was shown to proceed with high stereoselectivity (96–98% stereoselectivity under optimized conditions) thus allowing the preparation of substrates where the chiral silicon moiety can act as a chiral auxiliary for stereoselective transformations.
Trzoss, Michael