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

Andrew T Parsons; Matthew J Campbell; Jeffrey S Johnson

doi:10.1021/ol800819h

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

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

Authors

Andrew T Parsons¹, Matthew J Campbell, Jeffrey S Johnson

Affiliation

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

PMID: 18503280
DOI: 10.1021/ol800819h

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Cyclization
Cyclopropanes / chemistry*
Furans / chemical synthesis*
Molecular Structure
Palladium / chemistry*
Stereoisomerism
Vinyl Compounds / chemistry*

Substances

Cyclopropanes
Furans
Vinyl Compounds
Palladium