Mc. Carreno et al., INFLUENCE OF THE SULFINYL GROUP ON THE CHEMOSELECTIVITY AND PI-FACIALSELECTIVITY OF DIELS-ALDER REACTIONS OF (S)-2-(P-TOLYLSULFINYL)-1,4-BENZOQUINONE, Journal of organic chemistry, 61(2), 1996, pp. 503-509
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 diff
erent 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 di
ene. The high pi-facial selectivity observed could be controlled by ch
oosing adequate experimental conditions.