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

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Abstract
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.

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