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Issue 21, 2002
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Tandem radical addition–aldol condensations: evidence for the formation of zinc enolates in diethylzinc mediated radical additions to N-enoyloxazolidinones

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Abstract

Diethylzinc mediated addition of alkyl radicals to chiral N-enoyloxazolidinones is immediately followed by homolytic substitution at zinc leading to a zinc enolate; the trapping of the latter in a subsequent aldol condensation serves as a useful mechanistic probe; overall this reaction sequence constitutes a novel example of a one pot, three-component, radical-polar crossover reaction.

Graphical abstract: Tandem radical addition–aldol condensations: evidence for the formation of zinc enolates in diethylzinc mediated radical additions to N-enoyloxazolidinones

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Article information


Submitted
11 Jul 2002
Accepted
22 Aug 2002
First published
26 Sep 2002

Chem. Commun., 2002, 2506-2507
Article type
Communication

Tandem radical addition–aldol condensations: evidence for the formation of zinc enolates in diethylzinc mediated radical additions to N-enoyloxazolidinones

S. Bazin, L. Feray, D. Siri, J.-V. Naubron and M. P. Bertrand, Chem. Commun., 2002, 2506
DOI: 10.1039/B206695E

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