178043-05-5Relevant academic research and scientific papers
Synthesis and Diels-Alder reactions of N-(tert-butoxycarbonyl)-3-p-tolylsulfinyl-1-benzoquinone-4-imine
Bartolome, Jose M.,Carreno, M. Carmen,Urbano, Antonio
, p. 3187 - 3190 (1996)
The title compound was synthesized in 3 steps (regioselective sulfenylation, m-CPBA and Pb(OAc)4 oxidations) from N-Boc-p-anisidine. Its Diels-Alder reactions with cyclopentadiene took place on the double bonds C2-C3 or C5-C6 depending upon the experimental conditions with total endo-selectivity and high π-facial diastereoselectivity. The cycloaddition with trans-piperylene occurred exclusively on the sulfinylsubstituted dienophilic double bond C2-C3.
