α-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis

α-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis

New ketene equivalents, namely α‐haloenol acetates, are investigated as both nucleophilic and electrophilic reactants in a tandem aldol–lactonization reaction. Diethylaluminum ethoxide proves to be an efficient promoter for the aldol reaction with a wide range of substrates, including inter alia, al...

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Veröffentlicht in:European Journal of Organic Chemistry 2007-01, Vol.2007 (1), p.101-107
Hauptverfasser: Bejot, Romain, Anjaiah, Siddam, Falck, J. R., Mioskowski, Charles
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Sprache:eng
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Aldol reaction
Aluminum
Heterocycles
Lactonization
Tandem reaction
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container_end_page 107
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container_title European Journal of Organic Chemistry
container_volume 2007
creator Bejot, Romain
Anjaiah, Siddam
Falck, J. R.
Mioskowski, Charles
description New ketene equivalents, namely α‐haloenol acetates, are investigated as both nucleophilic and electrophilic reactants in a tandem aldol–lactonization reaction. Diethylaluminum ethoxide proves to be an efficient promoter for the aldol reaction with a wide range of substrates, including inter alia, aldehydes, ketones, imines, nitrones and oximes, leading to oxetan‐2‐ones, azetidin‐2‐ones and isoxazolidin‐5‐ones. The resultant heterocyclic adducts are common structural elements in numerous compounds of interest as well as key intermediates in the preparation of other functionalities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
doi_str_mv 10.1002/ejoc.200600708
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subjects Aldol reaction
Aluminum
Heterocycles
Lactonization
Tandem reaction
title α-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis
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