126497-16-3Relevant academic research and scientific papers
SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTIONS OF (S)-2-p-TOLYLSULFINYL-1,4-BENZOQUINONE
Carreno, M. Carmen,Ruano, Jose L. Garcia,Urbano, Antonio
, p. 4003 - 4006 (1989)
Optically pure (S)-2-p-tolylsulfinyl-1,4-benzoquinone (5) is readily obtained by deketalization of the corresponding quinone bisketal 4, synthesized by Andersen's type synthesis on 2-bromo-1,4-dimethoxybenzene (1) followed by anodic oxidation of the resulting sulfoxide.The Diels-Alder reaction of cyclopentadiene with 5 took place on C5-C6 dienophilic double bond showing high facial selectivity, which can be inverted by using different Lewis acids, and total endo selectivity.
