Enantioselective Bromo-oxycyclization of Silanol.

Org Lett 2016 Jan 14;18(1):80-3. Epub 2015 Dec 14.

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.

Relying on the nucleophilicity of silanol for building up silicon-incorporated scaffold with an enantiopure tetrasubstituted carbon center remains elusive. In this report, asymmetric bromo-oxycyclization of olefinic silanol by using chiral anionic phase-transfer catalyst is described. This protocol provided a facile entry to a wide arrangement of enantiopure benzoxasilole in moderate to excellent enantioselectivities depending on the unique reactivity of bromine/N-benzyl-DABCO complex.

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http://dx.doi.org/10.1021/acs.orglett.5b03303DOI Listing
January 2016
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