Tetrahedron Letters

BiBr 3, an efficient catalyst for the benzylation of alcohols: 2-phenyl-2-propyl, a new benzyl-type protecting group

B Boyer, EM Keramane, JP Roque, AA Pavia

Index: Boyer, Bernard; Keramane, El-Mehdi; Roque, Jean-Pierre; Pavia, Andre A. Tetrahedron Letters, 2000 , vol. 41, # 16 p. 2891 - 2894

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Citation Number: 33

Abstract

Numerous methods are available for protecting an alcohol moiety. 1 Conversion into the corresponding ethers has been recognized as a common and useful method for the protection of hydroxyl groups. Most commonly used are the tetrahydropyranyl (THP), 1-ethoxyethyl (EE), t-butyldimethylsilyl (TBDMS), benzyl (Bn) derivatives, etc. The experimental conditions used for benzylation being rather drastic (BnBr, DMSO, KOH), the need for a milder method is very important.