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

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

Volume: 3 Issue: 4

Author(s): Andrew G. H. Wee

Affiliation:

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

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.

Cite this article as:

H. Wee G. Andrew, Rhodium(II)-Catalyzed Reaction of Diazocompounds in the Service of Organic Synthesis of Natural and Non-Natural Products, Current Organic Synthesis 2006; 3 (4) . https://dx.doi.org/10.2174/157017906778699512