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Counterattack Mode Differential Acetylative Deprotection of Phenylmethyl Ethers: Applications to Solid Phase Organic Reactions

Asit K. Chakraborti* and Sunay V. Chankeshwara

*Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India, Email: akchakrabortiniper.ac.in

A. K. Chakraborti, S. V. Chankeshwara, J. Org. Chem., 2009, 74, 1367-1370.

DOI: 10.1021/jo801659g (free Supporting Information)


Abstract

A counterattack protocol for differential acetylative cleavage of phenylmethyl ether allows the reuse of the phenylmethyl moiety as benzyl bromide, thus providing advantages in terms of waste minimization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.


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proposed mechanism



Key Words

Benzylethers, Acetic Acid Esters


ID: J42-Y2009-0450