Alkylidenation of esters on solid support and traceless synthesis of 2-substituted benzofurans

Authors
Guthrie, EJ Macritchie, J Hartley, RC
Citation
Ej. Guthrie et al., Alkylidenation of esters on solid support and traceless synthesis of 2-substituted benzofurans, TETRAHEDR L, 41(25), 2000, pp. 4987-4990
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
25
Year of publication
2000
Pages
4987 - 4990
Database
ISI
SICI code
0040-4039(20000619)41:25<4987:AOEOSS>2.0.ZU;2-Q
Abstract
Polymer-supported esters are smoothly converted into enol ethers using a ti tanocene alkylidene prepared by treatment of 2-tert-butyldimethylsilyloxybe nzaldehyde diphenyldithioacetal with the low valent titanium species Cp2Ti[ P(OEt)(3)](2). Treatment of the enol ethers with acid leads to the release of ketones from the Wang resin in high yield. Traceless solid-phase synthes is of 2-substituted benzofurans is achieved in a three-step termination pro cedure. (C) 2000 Published by Elsevier Science Ltd.