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Issue 32, 2012

Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles

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Abstract

Heavily substituted cyclopropane esters were prepared in high yields, complete diastereoselection and high (up to 96%) enantioselectivity. The reaction described herein entailed reacting 4-nitro-5-styrylisoxazoles, a class of cinnamate synthetic equivalent, with 2-bromomalonate esters under the catalysis of 5 mol% of a Cincona derived phase-transfer catalyst. The reaction allowed multi-gram preparation of desired products.

Graphical abstract: Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles

Supplementary files

Article information


Submitted
17 Jan 2012
Accepted
23 Feb 2012
First published
24 Feb 2012

Chem. Commun., 2012,48, 3863-3865
Article type
Communication

Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles

C. D. Fiandra, L. Piras, F. Fini, P. Disetti, M. Moccia and M. F. A. Adamo, Chem. Commun., 2012, 48, 3863 DOI: 10.1039/C2CC30401E

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