4-Quinolylmethyl and 1-Naphthylmethyl as Benzyl-type Protecting Groups of Carboxylic Acids Removable by Homogeneous Palladium-Catalyzed Hydrogenolysis

✍ Scribed by André Boutros; Jean-Yves Legros; Jean-Claude Fiaud

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 243 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)01108-4

✦ Synopsis

AbstractÐ4-Quinolylmethyl (4-QUI) esters are reduced by palladium-catalyzed hydrogenolysis by formate anion. The reaction conditions are compatible with reducible substituents or functional groups as aromatic bromo, alkene, aldehyde, ketone, nitrile, ethyl and benzyl esters. An allyl ester is cleaved selectively in the presence of a 4-QUI ester. 1-Naphthylmethyl (1-NAP) esters of a-amino acids could be deprotected without any racemization by the same methodology.