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Synlett 1997; 1997(12): 1411-1413
DOI: 10.1055/s-1997-1062
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Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans by an Allyl Silane Metathesis - Nucleophilic Addition Sequence

John H. Cassidy1 , Stephen P. Marsden1 , Geoffrey Stemp2
  • 1Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY
  • 2SmithKline Beecham Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW
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Publication History

Publication Date:
31 December 2000 (online)

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Functionalised cyclic allyl silanes have been prepared by the ring closing metathesis of allyldimethylsilyl ethers of homoallylic alcohols. Treatment of these allyl silanes with aldehydes in the presence of boron trifluoride etherate gives high yields of 2,3,5-substituted tetrahydrofurans. Stereoselectivities are excellent for aldehydes with primary substituents, good for secondary substituents and modest for tertiary substituents.

allyl silane - metathesis - [3+2] annulation - tetrahydrofuran