Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to alpha-oxoketene dithioacetals: A facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation

Authors
Mehta, BK Nandi, S Ila, H Junjappa, H
Citation
Bk. Mehta et al., Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to alpha-oxoketene dithioacetals: A facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation, TETRAHEDRON, 55(44), 1999, pp. 12843-12852
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
44
Year of publication
1999
Pages
12843 - 12852
Database
ISI
SICI code
0040-4020(19991029)55:44<12843:HR1OAG>2.0.ZU;2-J
Abstract
4-Methoxybenzyl- (A), 3,4-dimethoxybenzyl- (B) and 3,4-methylenedioxybenzyl - (C) Grignard reagents are shown to undergo regioselective 1,2-addition wi th various acyclic and cyclic alpha-oxoketene dithioacetals to afford carbi nol dithioacetals which on BF3.Et2O catalyzed cyclization yield alkoxynapht halenes and their condensed derivatives in a highly regiocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.