4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis

被引：19

作者：

Boutros, A ^{[1
]}

Legros, JY ^{[1
]}

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol Orsay, Lab Catalyse Mol, CNRS,UPRESA 8075, F-91405 Orsay, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 15期

关键词：

catalysis; palladium and compounds; protecting groups; quinolines;

D O I：

10.1016/S0040-4020(99)01108-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-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 alpha-amino acids could be deprotected without any racemization by the same methodology. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2239 / 2246

页数：8

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