Chemoselective oxidative debenzylation of tertiary N-benzyl amines

被引：59

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：

CHEMICAL COMMUNICATIONS | 2000年 / 05期

关键词：

D O I：

10.1039/b000071j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of tertiary amines containing one or more N-benzyl protecting groups with aqueous ceric ammonium nitrate results in clean N-debenzylation to afford the corresponding secondary amine.

引用

页码：337 / 338

页数：2

共 43 条

[1] Development of a reductive alkylation method using p-benzyloxybenzylamine (BOBA) resin for the synthesis of N-alkylated amides [J].

Aoki, Y ;

Kobayashi, S .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (05) :371-372

[2]

BING Y, 1997, J ORG CHEM, V62, P9347

[3] Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate:: A practical method for the C-α epimerization of anti β-amino-α-hydroxy acids [J].

Brackenridge, I ;

Davies, SG ;

Fenwick, DR ;

Ichihara, O ;

Polywka, MEC .

TETRAHEDRON, 1999, 55 (02) :533-540

[4]

BRANDTNER S, 1999, TETRAHEDRON LETT, V11, P2105

[5] Synthesis of tertiary amines using a polystyrene (REM) resin [J].

Brown, AR ;

Rees, DC ;

Rankovic, Z ;

Morphy, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3288-3295

[6] AN EXPEDITIOUS ASYMMETRIC-SYNTHESIS OF ALLOPHENYLNORSTATINE [J].

BUNNAGE, ME ;

DAVIES, SG ;

GOODWIN, CJ ;

ICHIHARA, O .

TETRAHEDRON, 1994, 50 (13) :3975-3986

[7]

BUNNAGE ME, 1994, TETRAHEDRON-ASYMMETR, V5, P203

[8] ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID [J].

BUNNAGE, ME ;

BURKE, AJ ;

DAVIES, SG ;

GOODWIN, CJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :165-176

[9] ORIGINS OF THE HIGH STEREOSELECTIVITY IN THE CONJUGATE ADDITION OF LITHIUM(ALPHA-METHYLBENZYL)BENZYLAMIDE TO T-BUTYL CINNAMATE [J].

COSTELLO, JF ;

DAVIES, SG ;

ICHIHARA, O .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1999-2008

[10] Asymmetric synthesis of beta-amino acids via the Michael addition of chiral metal amides [J].

Davies, SG ;

Ichihara, O .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (01) :26-34

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