Issue 78, 2014

An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C–C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives

Abstract

An efficient enantioselective [3+2] cycloaddition of alkynes with oxiranes via selective C–C bond cleavage of epoxides was developed. A number of optically active 2,5-dihydrofurans were obtained in excellent yields (up to 99%) and enantioselectivities (up to 95% ee) under mild reaction conditions. Moreover, chiral tetrahydrofuran could also be obtained by cycloaddition of alkene and oxirane or hydrogenation of chiral 2,5-dihydrofuran.

Graphical abstract: An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C–C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives

Supplementary files

Article information

Article type
Communication
Submitted
31 May 2014
Accepted
04 Aug 2014
First published
05 Aug 2014

Chem. Commun., 2014,50, 11480-11483

An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C–C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives

W. Chen, X. Fu, L. Lin, X. Yuan, W. Luo, J. Feng, X. Liu and X. Feng, Chem. Commun., 2014, 50, 11480 DOI: 10.1039/C4CC04182H

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