Antimony pentachloride catalyzed Diels-Alder reactions: improved regioselectivity in the synthesis of dialkyl naphthoquinones

Authors
Nunes, RL Bieber, LW
Citation
Rl. Nunes et Lw. Bieber, Antimony pentachloride catalyzed Diels-Alder reactions: improved regioselectivity in the synthesis of dialkyl naphthoquinones, TETRAHEDR L, 42(2), 2001, pp. 219-221
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
2
Year of publication
2001
Pages
219 - 221
Database
ISI
SICI code
0040-4039(20010108)42:2<219:APCDRI>2.0.ZU;2-B
Abstract
Improved regioselectivity in catalyzed Diels-Alder (DA) cycloadditions betw een non-symmetrical benzoquinones and mono-substituted butadienes is achiev ed by use of SbCl5,. After oxidation, good yields of dialkylnaphthoquinones are obtained. The greater steric demand in comparison to other Lewis acids (LAs) seems to favor the less hindered transition state. (C) 2000 Elsevier Science Ltd. All rights reserved.