A new strategy for chemoselective O-acylation of β-mercapto alcohols via alkylsilyl and stannyl protection

Chemoselective preparation of O-acylated derivatives from bis-protected mercapto alcohols was described. Trialkylsilyl and trialkylstannyl chloride are used to generate an intermediate with O- and S-protection. The intermediates from beta-mercapto alcohols are reactive toward acylating agents and selective to provide O-acylated derivatives. The present preparation involves the direct conversion of alcohol to the corresponding O-acylated compounds without deprotection. (C) 2008 Elsevier Ltd. All rights reserved.