Base-Promoted Isomerization of cis-4-Formyl-2-azetidinones: Chemoselective C4-Epimerization vs...

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Bibliographic Details
Title: Base-Promoted Isomerization of cis-4-Formyl-2-azetidinones: Chemoselective C4-Epimerization vs...
Authors: Alcaide, Benito, Aly, Moustafa F.
Source: Journal of Organic Chemistry. 06/02/2000, Vol. 65 Issue 11, p3453. 7p. 9 Diagrams, 4 Charts.
Subjects: Lactams, Dimethylamine, Benzene, Phase-transfer catalysis, Rearrangements (Chemistry)
Abstract: Shows two simple, efficient and complementary methods for the regiospecific C4-epimerization of cis-4-formyl-2-azetidinones. Use of aqueous dimethylamine as reagent in heterogeneous medium with benzene; Presence of benzyltributylammonium bromide as the phase-transfer catalyst; Novel base-promoted rearrangement of the beta-lactam ring to cyclic enaminones.
Database: Engineering Source
Description
Abstract:Shows two simple, efficient and complementary methods for the regiospecific C4-epimerization of cis-4-formyl-2-azetidinones. Use of aqueous dimethylamine as reagent in heterogeneous medium with benzene; Presence of benzyltributylammonium bromide as the phase-transfer catalyst; Novel base-promoted rearrangement of the beta-lactam ring to cyclic enaminones.
ISSN:00223263
DOI:10.1021/jo991984h