Influence of the Sulfinyl Group on the Chemoselectivity and pi-Facial Selectivity of Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone.
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.
Carreño
M. Carmen
MC
Laboratoire de Cristallochimie, UA 424, Université Louis Pasteur, 67070 Strasbourg, France.
García Ruano
José L.
JL
Toledo
Miguel A.
MA
Urbano
Antonio
A
Remor
Cynthia Z.
CZ
Stefani
Valter
V
Fischer
Jean
J