Ring-opening and -expansion of 2,2′-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines

Authors

Stephen Bailey, University of WollongongFollow
Steven M. Wales, University of WollongongFollow
Anthony Willis, Australian National University
Paul Keller, University of WollongongFollow

RIS ID

92923

Publication Details

Bailey, S. J., Wales, S. M., Willis, A. C. & Keller, P. A. (2014). Ring-opening and -expansion of 2,2′-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines. Organic Letters, 16 (16), 4344-4347.

Abstract

The chiral pool-derived 1,1′-ditosyl-2,2′-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2′-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.