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

Research output: Contribution to journalArticle

20 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 languageEnglish
Pages (from-to)2064-2068
Number of pages5
JournalSynlett
Issue number13
DOIs
Publication statusPublished - Aug 1 2008

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Bentonite
Stereoselectivity
Acetals
Silicon
Glycosides
Scaffolds
Carbon
Alcohols
clay
silanol
C-glycoside

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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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.",
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