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Preparation of a `Si-centered' chiral auxiliary by resolution


Trzoss, Michael; Shao, Jie; Bienz, Stefan (2004). Preparation of a `Si-centered' chiral auxiliary by resolution. Tetrahedron: Asymmetry, 15(9):1501-1505.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:10 May 2004
Deposited On:23 Aug 2017 16:38
Last Modified:24 Aug 2017 07:32
Publisher:Elsevier
ISSN:0957-4166
Publisher DOI:https://doi.org/10.1016/j.tetasy.2004.03.014

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