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Org Lett. 2008 Jun 19;10(12):2541-4. doi: 10.1021/ol800819h. Epub 2008 May 27.

Diastereoselective synthesis of tetrahydrofurans via Palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes.

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  • 1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.

Abstract

Palladium(0)-catalyzed cycloadditions of malonate-derived vinylcyclopropane 1 and aldehydes to afford 2,5-cis disubstituted tetrahydrofuran derivatives are described. Pd loadings as low as 0.5 mol % were effective in catalyzing the transformation with high yields and diastereoselectivities. Electron-poor aldehydes work best, suggesting that a mechanism involving an initial aldol reaction may be operative.

PMID:
18503280
[PubMed - indexed for MEDLINE]
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