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

Journal Article


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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.

Publication Date


  • 2014

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84906266383

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3273&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2255

Number Of Pages


  • 3

Start Page


  • 4344

End Page


  • 4347

Volume


  • 16

Issue


  • 16

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.

Publication Date


  • 2014

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84906266383

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3273&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2255

Number Of Pages


  • 3

Start Page


  • 4344

End Page


  • 4347

Volume


  • 16

Issue


  • 16