SYNTHESIS AND DIELS-ALDER REACTIONS OF CARBONYL)-3-P-TOLYLSULFINYL-1-BENZOQUINONE-4-IMINE

Authors
BARTOLOME JM CARRENO MC URBANO A
Citation
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
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
18
Year of publication
1996
Pages
3187 - 3190
Database
ISI
SICI code
0040-4039(1996)37:18<3187:SADROC>2.0.ZU;2-D
Abstract
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