Novel alpha-substituted beta-amino diesters from acylnitroso-derived hetero-Diels-Alder cycloadducts

alpha-Methyl beta-amino diesters were synthesized in a simple three-step procedure starting from acylnitroso-derived Diels-Alder adducts of cyclopentadiene, Treatment of the cycloadducts with Copper catalyst-modified methylmagnesium bromide gave anti-1,2-cyclopentenyl hydroxamic acids. Reduction of...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 7; pp. 1131 - 1134
Main Authors Surman, MD, Mulvihill, MJ, Miller, MJ
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 11.02.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1 beta-methyl carbapenems
acylnitroso
ANALOGS
CARBAPENEM ANTIBIOTICS
Grignard
hydroxamic acid
beta-amino diesters
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Summary:alpha-Methyl beta-amino diesters were synthesized in a simple three-step procedure starting from acylnitroso-derived Diels-Alder adducts of cyclopentadiene, Treatment of the cycloadducts with Copper catalyst-modified methylmagnesium bromide gave anti-1,2-cyclopentenyl hydroxamic acids. Reduction of the hydroxmate N-O bond with titanium(III) chloride followed by ozonolytic cleavage of the cyclopentenyl olefin provided the desired alpha-methyl beta-amino diesters. (C) 2002 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)02353-X