Jm. Bartolome et al., SYNTHESIS AND DIELS-ALDER REACTIONS OF CARBONYL)-3-P-TOLYLSULFINYL-1-BENZOQUINONE-4-IMINE, Tetrahedron letters, 37(18), 1996, pp. 3187-3190
The title compound was synthesized in 3 steps (regioselective sulfenyl
ation, m-CPBA and Pb(OAc)(4) oxidations) from N-Boc-p-anisidine. Its D
iels-Alder reactions with cyclopentadiene took place on the double bon
ds C-2-C-3 or C-5-C-6 depending upon the experimental conditions with
total endo-selectivity and high pi-facial diastereoselectivity. The cy
cloaddition with trans-piperylene ocurred exclusively on the sulfinyls
ubstituted dienophilic double bond C-2-C-3. Copyright (C) 1996 Elsevie
r Science Ltd