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

页码：3765 / 3774

页数：10

共 62 条

[1] CERIC AMMONIUM-NITRATE IN ORGANIC-SYNTHESIS .2. OXIDATION OF N,N-DIMETHYL METHOXYPHENYLMETHYLAMINES TO METHOXYBENZALDEHYDES
BADEA, I
COTELLE, P
CATTEAU, JP
[J]. 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
BAJWA, JS
[J]. 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
Bajwa, JS
Slade, J
Repic, O
[J]. TETRAHEDRON LETTERS, 2000, 41 (32) : 6025 - 6028
[4] Novel cleavage of propargylamines by reaction with organolithium compounds
Barluenga, J
Canteli, RM
Florez, J
[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
Beaulieu, PL
Wernic, D
[J]. 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
BERNOTAS, RC
CUBE, RV
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (08) : 1209 - 1212
[8] BHATTACHARYYA S, 1995, SYNTHETIC COMMUN, V25, P2061
[9] NEW METHOD FOR METHYLATION OF AMINES
BORCH, RF
HASSID, AI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) : 1673 - &
[10] Bull SD, 2000, SYNLETT, P1257

← 1 2 3 4 5 6 7 →