Issue 21, 2018

Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

Abstract

A new type of donor–acceptor cyclopropane reactivity towards alkenes was revealed for 2-arylcyclopropane-1,1-diesters that contain an OH-group in the ortho-position of the aryl substituent. In this case, the initial cyclopropanes participate in formal (4 + 2)-cycloaddition as synthetic equivalents of ortho-quinone methides which are potential intermediates generated under mild conditions in the presence of a Lewis acid.

Graphical abstract: Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2018
Accepted
13 Mar 2018
First published
13 Mar 2018

Org. Biomol. Chem., 2018,16, 3897-3909

Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

K. L. Ivanov, S. I. Bezzubov, M. Ya. Melnikov and E. M. Budynina, Org. Biomol. Chem., 2018, 16, 3897 DOI: 10.1039/C8OB00377G

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