Influence of the Sulfinyl Group on the Chemoselectivity and pi-Facial Selectivity of Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone |
| |
Authors: | Carreño M Carmen García Ruano José L Toledo Miguel A Urbano Antonio Remor Cynthia Z Stefani Valter Fischer Jean |
| |
Institution: | Laboratoire de Cristallochimie, UA 424, Université Louis Pasteur, 67070 Strasbourg, France. |
| |
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: | |
本文献已被 PubMed 等数据库收录! |
|