Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones

María E. Ochoa, María S. Arias, Raúl Aguilar, Francisco Delgado, Joaquín Tamariz

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A short and regioselective synthesis of γ-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the α-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding γ-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided.
Original languageAmerican English
Pages (from-to)14535-14546
Number of pages13080
JournalTetrahedron
DOIs
StatePublished - 17 Dec 1999

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Cycloaddition Reaction
Alkenes
Hydrolysis
Derivatives
Oxidation
3-chloroperbenzoic acid
3-buten-2-one
ketene

Cite this

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title = "Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones",
abstract = "A short and regioselective synthesis of γ-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the α-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding γ-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided.",
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Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones. / Ochoa, María E.; Arias, María S.; Aguilar, Raúl; Delgado, Francisco; Tamariz, Joaquín.

In: Tetrahedron, 17.12.1999, p. 14535-14546.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones

AU - Ochoa, María E.

AU - Arias, María S.

AU - Aguilar, Raúl

AU - Delgado, Francisco

AU - Tamariz, Joaquín

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Y1 - 1999/12/17

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AB - A short and regioselective synthesis of γ-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the α-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding γ-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided.

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