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Conversion of α,β-epoxysilanes to silyl enol ethers; an unprecedented stereochemical result

✍ Scribed by Paul F. Hudrlik; Robert H. Schwartz; Ashok K. Kulkarni

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 244 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93684-6

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✦ Synopsis

Acyclic a,@-dihydroxysilanes (prepared from c@-epoxysilanes) react with KH to give silyl enol ethers; the predominant stereochemistry is consistent with anti elimination via d-oxidosilanes. We have recently shown that c&p-epoxysilanes can serve as stereospecific vinyl cation equivalents in the synthesis of olefins 2 and heteroatom-substituted olefins. 3 This synthesis is based on the finding that Oc,p-epoxysilanes undergo regioand stereospecific d-opening by a variety of nucleophiles to produce diastereomerically pure p-hydroxysilanes, 2-5 and that these p-hydroxysilanes undergo stereospecific syn or antip-elimination reactions under basic or acidic condi-

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