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Issue 3, 2014
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Intramolecular donor–acceptor cyclopropane ring-opening cyclizations

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Abstract

Cyclization reactions of donor–acceptor (D–A) cyclopropanes are recognized as versatile methods for construction of carbocyclic and heterocyclic scaffolds. In the literature, many examples of these polarized cyclopropanes' reactivity with nucleophiles, electrophiles, and radicals are prevalent. Although intermolecular reactivity of donor–acceptor cyclopropanes is widely reported, reviews that center on their intramolecular chemistry are rare. Thereupon, this tutorial review focalizes on new intramolecular transformations of donor–acceptor cyclopropanes for cycloisomerizations, formal cycloadditions, umpolung reactions, rearrangements and ring-opening lactonizations/lactamizations from 2009 to 2013. Furthermore, the role of D–A acceptor cyclopropanes as reactive subunits in natural product synthesis is underscored.

Graphical abstract: Intramolecular donor–acceptor cyclopropane ring-opening cyclizations

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Article information


Submitted
05 Jul 2013
First published
21 Nov 2013

Chem. Soc. Rev., 2014,43, 804-818
Article type
Tutorial Review

Intramolecular donor–acceptor cyclopropane ring-opening cyclizations

M. A. Cavitt, L. H. Phun and S. France, Chem. Soc. Rev., 2014, 43, 804
DOI: 10.1039/C3CS60238A

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