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

Stephen J. Bailey, Steven M. Wales, Anthony C. Willis, Paul A. Keller*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4344-4347
Number of pages4
JournalOrganic Letters
Volume16
Issue number16
DOIs
Publication statusPublished - 15 Aug 2014

Fingerprint

Dive into the research topics of 'Ring-opening and -expansion of 2,2′-biaziridine: Access to diverse enantiopure linear and bicyclic vicinal diamines'. Together they form a unique fingerprint.

Cite this