Arylmethyl esters as protecting groups for carboxylic, carbonic and carbamic acids: deprotection via homogeneous palladium-catalyzed hydrogenolysis

被引:15
作者
Boutros, A [1 ]
Legros, JY [1 ]
Fiaud, JC [1 ]
机构
[1] Univ Paris 11, CNRS, Lab Catalyse Mol, UPRESA 8075,Inst Chim Mol Orsay, F-91405 Orsay, France
关键词
catalysis; palladium; palladium compounds; protecting groups; quinolines;
D O I
10.1016/S0040-4039(99)01457-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Quinolylmethyl (4-QUI) esters of carboxylic acids and 1-naphthylmethyl (1-NAP) esters of carbonic and carbamic acids are reduced by palladium-catalyzed hydrogenolysis by formate anion. The reaction conditions are compatible with the presence of a benzyl ester and of an alkene double bond. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7329 / 7332
页数:4
相关论文
共 8 条
[1]   Preferential hydrogenolysis of NAP esters provides a new orthogonal protecting group strategy for carboxylic acids [J].
Gaunt, MJ ;
Boschetti, CE ;
Yu, JQ ;
Spencer, JB .
TETRAHEDRON LETTERS, 1999, 40 (09) :1803-1806
[2]  
GREENE TW, 1991, PROTECTIVE GROUPS OR
[3]   Allylic protecting groups and their use in a complex environment -: Part II:: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology [J].
Guibé, F .
TETRAHEDRON, 1998, 54 (13) :2967-3042
[4]  
Kocienski P.J., 1994, PROTECTING GROUPS
[5]   PALLADIUM-CATALYZED SUBSTITUTION OF ESTERS OF NAPHTHYLMETHANOLS, 1-NAPHTHYLETHANOLS, AND ANALOGS BY SODIUM DIMETHYL MALONATE - STEREOSELECTIVE SYNTHESIS FROM ENANTIOMERICALLY PURE SUBSTRATES [J].
LEGROS, JY ;
TOFFANO, M ;
FIAUD, JC .
TETRAHEDRON, 1995, 51 (11) :3235-3246
[6]   PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF NAPHTHYLMETHYL AND 1-NAPHTHYLETHYL ESTERS [J].
LEGROS, JY ;
FIAUD, JC .
TETRAHEDRON LETTERS, 1992, 33 (18) :2509-2510
[7]   ASYMMETRIC PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF RACEMIC 1-NAPHTHYLETHYL ESTERS [J].
LEGROS, JY ;
TOFFANO, M ;
FIAUD, JC .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1899-1902
[8]  
Tsuji J., 1995, PALLADIUM REAGENTS C