Journal article
Ring-Opening and -Expansion of 2,2 '-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
Organic Letters, Vol.16(16), pp.4344-4347
2014
PMID: 25101915
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.
Details
- Title
- Ring-Opening and -Expansion of 2,2 '-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
- Authors
- Stephen J. Bailey (Author) - University of WollongongSteven M. Wales (Author) - University of WollongongAnthony C. Willis (Author) - Australian National UniversityPaul A. Keller (Corresponding Author) - University of Wollongong
- Publication details
- Organic Letters, Vol.16(16), pp.4344-4347
- Publisher
- American Chemical Society
- DOI
- 10.1021/ol502164b
- ISSN
- 1523-7052
- PMID
- 25101915
- Organisation Unit
- Student Services and Engagement; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99707483702621
- Output Type
- Journal article
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- Domestic collaboration
- Web Of Science research areas
- Chemistry, Organic
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