One-step syntheses of substituted 2-pyrrolidinones and 3-pyrrolidinones from α,β-unsaturated diazoketones and amines. Application in the synthesis of barmumycin

A simple and one-pot way to prepare substituted 2- and 3-pyrrolidinones is described. The method uses unsaturated diazoketones (obtained from aldeydes in a single step) and amines, and provide an easy access to these important classes of nitrogen heterocycles. Furthermore, application of this method...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 26; pp. 3720 - 3729
Main Authors Dias, Rafael M.P., Momo, Patrícia B., Burtoloso, Antonio C.B.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.06.2017
Elsevier
Subjects
Barmumycin
Chemistry
Chemistry, Organic
Diazo compounds
Michael addition
Physical Sciences
Pyrrolidines
Science & Technology
Wolff rearrangement
Michael addition
Pyrrolidines
Barmumycin
Diazo compounds
Wolff rearrangement
ORGANIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
PREUSSIN
N-H
PYRROLIDINE DERIVATIVES
O-H
H INSERTION REACTIONS
DIAZOACETOACETATE
ALKALOIDS
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Summary:A simple and one-pot way to prepare substituted 2- and 3-pyrrolidinones is described. The method uses unsaturated diazoketones (obtained from aldeydes in a single step) and amines, and provide an easy access to these important classes of nitrogen heterocycles. Furthermore, application of this methodology to the synthesis of the natural product barmumycin is achieved in 3 steps from these diazoketones. [Display omitted]
Bibliography:FAPESP
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.05.040