1020186-13-3Relevant academic research and scientific papers
New reagents for the synthesis of arylmethyl ethers and esters
Albiniak, Philip A.,Dudley, Gregory B.
scheme or table, p. 841 - 851 (2010/07/10)
This Account chronicles efforts leading up to the development of new arylmethyl transfer (benzylation) reagents for protecting oxygen functional groups under relatively mild and neutral conditions. It begins with an investigation of organosiletanes as surrogate hydroxyl groups, which inspired siletane-functionalized benzyl ethers and forced us to confront the difficulties associated with the synthesis of benzyl ethers. The end result is a new series of neutral oxypyridinium salts for the benzylation of various nucleophilic functional groups under mild conditions. 1 Introduction 2 Tamao-type Oxidation of Strained Organosiletanes 3 p-Siletanylbenzyl (PSB) Protecting Groups 4 2-Benzyloxy-1-methylpyridinium Triflate 5 Friedel-Crafts Reactions and Mechanistic Insights 6 Benzyl Ester Formation 7 Substituted Benzyl Transfer Reagents 8 Conclusions and Outlook. Georg Thieme Verlag Stuttgart New York.
An efficient means for generating p-methoxybenzyl (PMB) ethers under mildly acidic conditions
Stewart, Catherine A.,Peng, Xiaowen,Paquette, Leo A.
, p. 433 - 437 (2008/09/20)
The protection of a wide variety of alcohols as their p-methoxybenzyl ethers can be performed with PMBO-lepidine in the presence of methyl tosylate or, preferably, camphorsulfonic acid. No inorganic promoters are required, thereby facilitating workup and product isolation. Georg Thieme Verlag Stuttgart.
