Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (2), 503-509
- https://doi.org/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.Keywords
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