Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines | Zendy

S. Bailey | Zendy; Steven M. Wales | Zendy; Anthony C. Willis | Zendy; Paul A. Keller | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines

Author(s) -

S. Bailey,

Steven M. Wales,

Anthony C. Willis,

Paul A. Keller

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502164b

Subject(s) - enantiopure drug , chemistry , vicinal , bicyclic molecule , regioselectivity , nucleophile , ring (chemistry) , desymmetrization , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research