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Rhodium(II)-Catalyzed Reaction of Diazocompounds in the Service of Organic Synthesis of Natural and Non-Natural Products

[ Vol. 3 , Issue. 4 ]

Author(s):

Andrew G. H. Wee   Pages 499 - 555 ( 57 )

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

Affiliation:

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



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