Work

Synthesis of Chiral Aziridines Through Decarboxylative Generation of Sulfur Ylides and Their Reaction with Chiral Sulfinyl Imines

Year: 2009

Type: article

Abstract: Reaction of sulfur ylide with a series of aryl substituted chiral non-racemic sulfinyl imines afforded the corresponding aziridines in high yield and good stereoselection. The sulfur ylides were generated by the thermally induced decarboxylation of carboxymethylsulfonium betaines. A drop in the diastereomeric ratio was observed when going from electron deficient to electron releasing aryl substituted imines. Sulfonium methylidene aziridinations involving the decarboxylation of carboxymethylsulfonium betaine functionality compliments existing technologies with the advantages of the reaction protocol, levels of conversion and scope.

Source: Synthetic Communications

DOI: 10.1080/00397910802654898

Authors: David C. Forbes, Sampada V. Bettigeri, Sejal R. Amin, Christie J. Bean, Amanda M. Law, Robert A. Stockman

Institutions: University of South Alabama, University of Nottingham

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Engineering and Physical Sciences Research Council, National Institute of General Medical Sciences

Awards: G3208458830, Application of Sulfurane Chemistry in the Assembly of HIV Protease Inhibitors, G7188606155