Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

被引:91
作者
Bull, SD
Davies, SG
Fenton, G
Mulvaney, AW
Prasad, RS
Smith, AD
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Rhone Poulenc Rorer, Dagenham RM10 7XS, Essex, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 22期
关键词
D O I
10.1039/b006852g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of a range of N-benzyl tertiary amines with aqueous ceric ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-N-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and S-benzyl ethers.
引用
收藏
页码:3765 / 3774
页数:10
相关论文
共 62 条
[1]   CERIC AMMONIUM-NITRATE IN ORGANIC-SYNTHESIS .2. OXIDATION OF N,N-DIMETHYL METHOXYPHENYLMETHYLAMINES TO METHOXYBENZALDEHYDES [J].
BADEA, I ;
COTELLE, P ;
CATTEAU, JP .
SYNTHETIC COMMUNICATIONS, 1994, 24 (14) :2011-2016
[2]   CHEMOSELECTIVE DEPROTECTION OF BENZYL-ESTERS IN THE PRESENCE OF BENZYL ETHERS, BENZYLOXYMETHYL ETHERS AND N-BENZYL GROUPS BY CATALYTIC TRANSFER HYDROGENATION [J].
BAJWA, JS .
TETRAHEDRON LETTERS, 1992, 33 (17) :2299-2302
[3]   Chemoselective deprotection of tertiary benzylamines and reduction of carbon-carbon double bonds in the presence of benzyl and benzyloxymethyl ethers [J].
Bajwa, JS ;
Slade, J ;
Repic, O .
TETRAHEDRON LETTERS, 2000, 41 (32) :6025-6028
[4]   Novel cleavage of propargylamines by reaction with organolithium compounds [J].
Barluenga, J ;
Canteli, RM ;
Florez, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3646-3649
[5]   Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors [J].
Beaulieu, PL ;
Wernic, D .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3635-3645
[6]  
BENARAB A, 1994, HETEROCYCLES, V38, P1641
[7]   THE USE OF PEARLMAN CATALYST FOR SELECTIVE N-DEBENZYLATION IN THE PRESENCE OF BENZYL ETHERS [J].
BERNOTAS, RC ;
CUBE, RV .
SYNTHETIC COMMUNICATIONS, 1990, 20 (08) :1209-1212
[8]  
BHATTACHARYYA S, 1995, SYNTHETIC COMMUN, V25, P2061
[9]   NEW METHOD FOR METHYLATION OF AMINES [J].
BORCH, RF ;
HASSID, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) :1673-&
[10]  
Bull SD, 2000, SYNLETT, P1257