Functionalized γ-lactones via intramolecular nitrile oxide cycloaddition

Giuseppe Buemi; Ugo Chiacchio; Antonino Corsaro; Giovanni Romeo; Antonio Rescifina; Nicola Uccella; Alfred Hassner

doi:10.3987/com-93-6376

Functionalized γ-lactones via intramolecular nitrile oxide cycloaddition

Giuseppe Buemi, Ugo Chiacchio, Antonino Corsaro, Giovanni Romeo, Antonio Rescifina, Nicola Uccella, Alfred Hassner

Department of Chemistry

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9 Scopus citations

Abstract

The intramolecular nitrile oxide cycloaddition of a series of unsaturated hydroxyimino esters has been investigated. The reaction has been found to be stereospecific, with the configuration of the reacting double bond maintained in the final product. Lack of intramolecular pathway has been observed when R, R₁ or R₂ are hydrogen atoms. AM1 calculation help rationalizes the observed reactions.

Original language	English
Pages (from-to)	2005-2018
Number of pages	14
Journal	Heterocycles
Volume	36
Issue number	9
DOIs	https://doi.org/10.3987/com-93-6376
State	Published - 1 Sep 1993

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abstract = "The intramolecular nitrile oxide cycloaddition of a series of unsaturated hydroxyimino esters has been investigated. The reaction has been found to be stereospecific, with the configuration of the reacting double bond maintained in the final product. Lack of intramolecular pathway has been observed when R, R1 or R2 are hydrogen atoms. AM1 calculation help rationalizes the observed reactions.",

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AU - Buemi, Giuseppe

AU - Chiacchio, Ugo

AU - Corsaro, Antonino

AU - Romeo, Giovanni

AU - Rescifina, Antonio

AU - Uccella, Nicola

AU - Hassner, Alfred

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AB - The intramolecular nitrile oxide cycloaddition of a series of unsaturated hydroxyimino esters has been investigated. The reaction has been found to be stereospecific, with the configuration of the reacting double bond maintained in the final product. Lack of intramolecular pathway has been observed when R, R1 or R2 are hydrogen atoms. AM1 calculation help rationalizes the observed reactions.

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Functionalized γ-lactones via intramolecular nitrile oxide cycloaddition

Abstract

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