Nucleophilic Deprotection of <i>p</i>-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst

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  • Ikeda Rei
    Graduate School of Pharmaceutical Sciences, Osaka University
  • Nishio Tomoya
    Graduate School of Pharmaceutical Sciences, Osaka University
  • Kanomata Kyohei
    Graduate School of Pharmaceutical Sciences, Osaka University
  • Akai Shuji
    Graduate School of Pharmaceutical Sciences, Osaka University

Abstract

<p>Nucleophilic deprotection of p-methoxybenzyl (PMB) [p-methoxyphenylmethyl (MPM)] ethers was developed using a heterogeneous oxovanadium catalyst V-MPS4 and a thiol nucleophile. The deprotection method had a wide reaction scope, including PMB ethers of primary, secondary, and tertiary alcohols bearing various functional groups. In addition, the PMB ether of an oxidation-labile natural product was successfully removed by V-MPS4 catalysis, while a common oxidative method of PMB deprotection afforded a complex mixture. The V-MPS4 catalyst was reusable up to six times without a significant loss in the product yield. The advantages of using the heterogeneous catalyst were further demonstrated by conducting the deprotection reaction in a continuous flow process, which resulted in a 2.7-fold higher catalyst turnover number and 60-fold higher turnover frequency compared to those of the corresponding batch reaction.</p>

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