Application of Donor/Acceptor-Carbenoids to the Synthesis of Natural Products

• Type of Material: Article
• Authors: Huw Davies, Emory University; Justin R. Denton, State University of New York
• Language: English
• Date: 2009-11
• Publisher: Royal Society of Chemistry
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: This journal is © The Royal Society of Chemistry 2009
• Final Published Version (URL): http://pubs.rsc.org/en/Content/ArticleLanding/2009/CS/b901170f
• Title of Journal or Parent Work: Chemical Society Reviews
• ISSN: 0306-0012
• Volume: 38
• Issue: 11
• Start Page: 3061
• End Page: 3071
• Grant/Funding Information: Financial support of this work by the National Institutes of Health (GM080337) and the National Science Foundation (CHE-0750273) is gratefully acknowledged.
• Keywords: donor/acceptor carbenoids; metal-carbenoid intermediate; structural complexity; organic synthesis; cascade sequence; metal catalyzed reaction; diazo compounds
• Research Categories: Chemistry, General; Chemistry, Organic

Abstract

The metal catalyzed reactions of diazo compounds have been broadly used in organic synthesis. The resulting metal-carbenoid intermediates are capable of undergoing a range of unconventional reactions, and due to their high energy, they are ideal for initiating a cascade sequence leading to rapid the rapid generation of structural complexity. This tutorial review will be give an overview of the most versatile reactions of donor/acceptor carbenoids, an exciting class of intermediates capable of highly selective reactions. This will include cyclopropanation, [4 + 3] cycloaddition, and C–H functionalization methodologies. The application of this chemistry to the synthesis of a range of natural products will be described.