α-haloenol acetates: Versatile reactants for oxetan-2-one, azetidin-2-one and isoxazolidin-5-one synthesis

Romain Bejot; Siddam Anjaiah; J R Falck; Charles Mioskowski

doi:10.1002/ejoc.200600708

α-haloenol acetates: Versatile reactants for oxetan-2-one, azetidin-2-one and isoxazolidin-5-one synthesis

Romain Bejot, Siddam Anjaiah, J R Falck, Charles Mioskowski

Biochemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	101-107
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.200600708
State	Published - Jan 1 2007

Keywords

Aldol reaction
Aluminum
Heterocycles
Lactonization
Tandem reaction

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200600708

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abstract = "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.",

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T2 - Versatile reactants for oxetan-2-one, azetidin-2-one and isoxazolidin-5-one synthesis

AU - Bejot, Romain

AU - Anjaiah, Siddam

AU - Falck, J R

AU - Mioskowski, Charles

PY - 2007/1/1

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N2 - 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.

AB - 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.

KW - Aldol reaction

KW - Aluminum

KW - Heterocycles

KW - Lactonization

KW - Tandem reaction

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α-haloenol acetates: Versatile reactants for oxetan-2-one, azetidin-2-one and isoxazolidin-5-one synthesis

Abstract

Keywords

ASJC Scopus subject areas

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