713514-50-2Relevant academic research and scientific papers
Preparation of a 'Si-centered' chiral auxiliary by resolution
Trzoss, Michael,Shao, Jie,Bienz, Stefan
, p. 1501 - 1505 (2004)
(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.
