Influence of the Sulfinyl Group on the Chemoselectivity and pi-Facial Selectivity of Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

M. Carmen Carreño; José L. García Ruano; Miguel A. Toledo; Antonio Urbano; Cynthia Z. Remor; Valter Stefani; Jean Fischer

doi:10.1021/jo951438y

Influence of the Sulfinyl Group on the Chemoselectivity and pi-Facial Selectivity of Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

J Org Chem. 1996 Jan 26;61(2):503-509. doi: 10.1021/jo951438y.

Authors

M. Carmen Carreño¹, José L. García Ruano, Miguel A. Toledo, Antonio Urbano, Cynthia Z. Remor, Valter Stefani, Jean Fischer

Affiliation

¹ Laboratoire de Cristallochimie, UA 424, Université Louis Pasteur, 67070 Strasbourg, France.

PMID: 11666967
DOI: 10.1021/jo951438y

Abstract

Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C(2)-C(3) versus C(5)-C(6) double bonds) is mainly related to the cyclic (on C(5)-C(6)) or acyclic (on C(2)-C(3)) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.