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

• Authors: Huw Davies, Emory University; Justin R. Denton, State University of New York
• Journal Title: Chemical Society Reviews
• Volume: Volume 38, Number 11
• Publisher: Royal Society of Chemistry | 2009-11, Pages 3061-3071
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1039/b901170f
• Subjects: Chemistry, General; Chemistry, Organic
• Keywords: metal catalyzed reaction; diazo compounds; organic synthesis; metal-carbenoid intermediate; cascade sequence; structural complexity; donor/acceptor carbenoids

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.