CLEAVAGE OF MEM ETHERS BY TETRAHALOZINCATE REAGENTS

Citation
Jm. Herbert et al., CLEAVAGE OF MEM ETHERS BY TETRAHALOZINCATE REAGENTS, Tetrahedron, 52(48), 1996, pp. 15257-15266
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
52
Issue
48
Year of publication
1996
Pages
15257 - 15266
Database
ISI
SICI code
0040-4020(1996)52:48<15257:COMEBT>2.0.ZU;2-I
Abstract
A modification of the zinc halide-mediated removal of the MEM group is described. By the expedient of adding two molar equivalents of ethere al hydrogen chloride or of lithium halide, the method is extended to s ubstrates which otherwise chelate the zinc reagent without undergoing deprotection. The compatibility of the resulting reagent systems with other functional groups is demonstrated, and examples are presented wh ere deprotection of mono-MEM-protected 1,2- and 1,3-diols can be carri ed out, avoiding the cyclisation which occurs normally. Copyright (C) 1996 Elsevier Science Ltd