Intramolecular donor-acceptor cyclopropane ring-opening cyclizations

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....

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Bibliographic Details
Published in:Chemical Society reviews 2014-02, Vol.43 (3), p.84-818
Main Authors: Cavitt, Marchello A, Phun, Lien H, France, Stefan
Format: Article
Language:English
Online Access:Get full text
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Summary: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. This tutorial review focalizes on recent intramolecular transformations of donor-acceptor cyclopropanes for cycloisomerizations, cycloadditions, umpolung reactions, rearrangements, and ring-opening lactonizations.
ISSN:0306-0012
1460-4744
DOI:10.1039/c3cs60238a