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ChemInform Abstract: Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans by an Allyl Silane Metathesis — Nucleophilic Addition Sequence.

✍ Scribed by J. H. CASSIDY; S. P. MARSDEN; G. STEMP

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199815098

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✦ Synopsis

Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans by an Allyl Silane Metathesis -Nucleophilic Addition Sequence.

-Ring closing metathesis of allyldimethylsilyl ethers (I) of homoallylic alcohols gives functionalized cyclic allyl silanes (II). They react with aldehydes in the presence of a Lewis acid to yield 2,3,5-trisubstituted tetrahydrofurans. Best results are obtained under conditions A). Diastereoselectivities are excellent for primary substituents and modest for tertiary substituents. -(CASSIDY, J.

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