Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol

Atsuo Nakazaki; Junji Usuki; Katsuhiko Tomooka

doi:10.1055/s-2008-1077953

Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol

Atsuo Nakazaki, Junji Usuki, Katsuhiko Tomooka

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-Å MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.

Original language	English
Pages (from-to)	2064-2068
Number of pages	5
Journal	Synlett
Issue number	13
DOIs	https://doi.org/10.1055/s-2008-1077953
Publication status	Published - Aug 1 2008

All Science Journal Classification (ASJC) codes

Organic Chemistry

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abstract = "The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-{\AA} MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.",

author = "Atsuo Nakazaki and Junji Usuki and Katsuhiko Tomooka",

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AU - Usuki, Junji

AU - Tomooka, Katsuhiko

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AB - The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-Å MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.

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Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol

Abstract

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