Reactivity and selectivity of captodative olefins as dienes in hetero-Diels-Alder reactions

Rubén Sanabria, Rafael Herrera, Raúl Aguilar, Carlos González-Romero, Hugo A. Jiménez-Vázquez, Francisco Delgado, Björn C.G. Söderberg, Joaquín Tamariz

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reactivity and selectivity of the the captodative olefins 1-acylvinyl benzoates 1a-1f and 3a as heterodienes in hetero-Diels-Alder reactions in the presence of electron-rich dienophiles is described. Heterodienes 1 undergo regioselective cycloaddition with the alkyl vinyl etherdienophiles 6a,b and 9 to give the corresponding dihydro-2H-pyrans 7, 8, and 10 under thermal conditions. The reactivity of these cycloadditions depends, to a large extent, on the electronic demand of the substituent in the aroyloxy group of the heterodiene. Frontier-molecular-orbital (FMO; ab initio) and density-functional-theory (DFT) calculations of the ground and transition states account for the reactivity and regioselectivity observed in these processes. © 2008 Verlag Helvetica Chimica Acta AG.
Original languageAmerican English
Pages (from-to)1807-1827
Number of pages1624
JournalHelvetica Chimica Acta
DOIs
StatePublished - 1 Jan 2008

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Diels-Alder reactions
Cycloaddition
Cycloaddition Reaction
Alkenes
dienes
alkenes
Olefins
reactivity
selectivity
cycloaddition
Pyrans
Regioselectivity
Benzoates
Molecular orbitals
Density functional theory
Electrons
molecular orbitals
Hot Temperature
density functional theory
ground state

Cite this

Sanabria, Rubén ; Herrera, Rafael ; Aguilar, Raúl ; González-Romero, Carlos ; Jiménez-Vázquez, Hugo A. ; Delgado, Francisco ; Söderberg, Björn C.G. ; Tamariz, Joaquín. / Reactivity and selectivity of captodative olefins as dienes in hetero-Diels-Alder reactions. In: Helvetica Chimica Acta. 2008 ; pp. 1807-1827.
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Reactivity and selectivity of captodative olefins as dienes in hetero-Diels-Alder reactions. / Sanabria, Rubén; Herrera, Rafael; Aguilar, Raúl; González-Romero, Carlos; Jiménez-Vázquez, Hugo A.; Delgado, Francisco; Söderberg, Björn C.G.; Tamariz, Joaquín.

In: Helvetica Chimica Acta, 01.01.2008, p. 1807-1827.

Research output: Contribution to journalArticle

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AU - Sanabria, Rubén

AU - Herrera, Rafael

AU - Aguilar, Raúl

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AU - Jiménez-Vázquez, Hugo A.

AU - Delgado, Francisco

AU - Söderberg, Björn C.G.

AU - Tamariz, Joaquín

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