Modulation of ?-Facial Selectivity in Diels-Alder Cycloaddition to Isodicyclopentafulvenes by Remote Para Substitution of an Exocyclic Phenyl Group

DOI: 10.1021/jo00243a054

Source and publish data:

Journal of Organic Chemistry p. 1835 - 1837 (1988)

Update date:2022-08-03

Topics:

Authors:

Paquette, Leo A.

Gugelchuk, Melinda

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Article abstract of DOI:10.1021/jo00243a054

Isodicyclopentafulvenes that carry an exocyclic para-substituted phenyl group as in 3 enter into Diels-Alder cycloaddition with highly reactive dienophiles exclusively from below-plane.The situation with the more sterically hindered and less reactive reagent (Z)-1,2-bis(phenylsulfonyl)ethylene is one where addition occurs from both faces.

Full text of DOI:10.1021/jo00243a054

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