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Reactivity and Selectivity of Captodative Olefins as Dienes in Hetero-Diels–Alder Reactions

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

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
435 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

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‐2__H__‐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.

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