2001 protection, deprotection

protection, deprotectionO 0345

13 - 073Chemoselective Debenzylation of N-Benzyl Tertiary Amines withCeric Ammonium Nitrate. — The title reaction proceeds successfullyunder conditions A) in the presence of N-benzylamides, O-benzyl ethers, esters,phenolates and S-benzyl ethers. Attempted deprotection is unsuccessful in thecase of (Vc), (Vd) and cyclic tertiary N-benzyl amines [cf. (VII), (IX)(recoveryof starting material) and (XI)(polymerization)]. The secondary amine productsare inert to further oxidation. — (BULL, STEVEN D.; DAVIES, STEPHENG.; FENTON, GARRY; MULVANEY, ANDREW W.; PRASAD, R. SHYAM;SMITH, ANDREW D.; Perkin 1 (2000) 22, 3765-3774; Dyson Perrins Lab.,Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK; EN)

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