Azasugar analogues: conformationally restricted vicinal diamine derived from ( S)-(−)-pyroglutamic acid

The preparation of a diamino substituted pyrrolidinone system in a diastereoselectively controlled manner is described. The procedure employed made use of electrophilic amination of a chiral bicyclic γ-lactam, which when subjected to sequential deprotection provided a simple route to a 3,4-diaminopy...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-10, Vol.10 (20), p.3887-3891
Main Authors: Chan, Philip W.H., Cottrell, Ian F., Moloney, Mark G.
Format: Article
Language:English
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Summary:The preparation of a diamino substituted pyrrolidinone system in a diastereoselectively controlled manner is described. The procedure employed made use of electrophilic amination of a chiral bicyclic γ-lactam, which when subjected to sequential deprotection provided a simple route to a 3,4-diaminopyroglutaminol. The chemoselective deprotection of the amino functionality was also shown to be possible under mild hydrogenolytic conditions.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00420-6