Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Stereoselective Synthesis via Palladium-Catalyzed Intramolecular Bis-Silylation
Michinori SuginomeYoshihiko Ito
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1997 Volume 55 Issue 11 Pages 1040-1051

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Abstract

Stereoselective intramolecular bis-silylation reactions catalyzed by isonitrile-palladium (O) complexes are described. Their useful synthetic applications were demonstrated by stereoselective asymmetric synthesis of a natural product and building blocks, e.g., (-) -avenaciolide was synthesized from (R) -3-vinyl-1-undecen-4-ol, and highly enantio-enriched allylsilanes and allenylsilanes were synthesized from the corresponding optically active allylic and propargylic alcohols, respectively. Attempts at catalytic intramolecular asymmetric bis-silylation with optically active t-alkyl isocyanide complexes are also described.

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© The Society of Syhthetic Organic Chemistry, Japan
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