Author: H. Wee, Andrew G.

Source: Current Organic Synthesis, Volume 3, Number 4, November 2006 , pp. 499-555(57)

Publisher: Bentham Science Publishers

Abstract:

The rhodium(II)-carbenoid mediated transformation of diazocarbonyl compounds is well recognized as a useful process for the facile formation of carbon-carbon and carbon-heteroatom bonds under mild reaction conditions. In this review, the incorporation of rhodium(II)-carbenoid transformations in the synthetic planning and the eventual application of rhodium(II) carbenoid reactions in the synthesis of natural products, non-natural compounds of medicinal importance, and advanced intermediates are discussed. Focus is placed on the use of intermolecular and intramolecular C-H and X-H insertion, intermolecular and intramolecular cyclopropanation, and tandem ylide (carbonyl, ammonium, oxonium, sulfonium) formation/1,3-dipolar cycloaddition, [2,3]-sigmatropic or Stevens [1,2]-rearrangement reactions as key step(s) in the synthetic routes.

Keywords: Rhodium-carbenoid; insertion; cyclopropanation; ylide; enantioselective; diastereoselective; synthesis; metallocarbene

Document Type: Research article

DOI: http://dx.doi.org/10.2174/157017906778699512

Affiliations: 1: Department of Chemistry and Biochemistry, University of Regina, Regina, Saskatchewan, S4S 0A2, Canada.

Publication date: 2006-11-01

More about this publication?

• Current Organic Synthesis publishes in-depth reviews on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.

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