Electrophilic amination of carbanions by N-carboxamido oxaziridines

被引：29

作者：

Armstrong, A ^{[1
]}

Atkin, MA

Swallow, S

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

amination; oxaziridines; carbanions; amino acids and derivatives; ureas;

D O I：

10.1016/S0040-4039(00)00140-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of 3-aryl-N-carboxamido oxaziridines have been prepared and tested as reagents for electrophilic amination of carbanions. The 3-(2-cyanophenyl)-derivative gave highest yields of amination product, and was used for amination of ketone, eater and amide enolates, as well as sulfone-, phosphonate- and nitrile-stabilized carbanions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2247 / 2251

页数：5

共 15 条

[11] N-Boc-3-trichloromethyloxaziridine: A new, powerful reagent for electrophilic amination [J].

Vidal, J ;

Hannachi, JC ;

Hourdin, G ;

Mulatier, JC ;

Collet, A .

TETRAHEDRON LETTERS, 1998, 39 (48) :8845-8848

[12] ELECTROPHILIC AMINATION REAGENTS - A NEW METHOD FOR THE PREPARATION OF 3-ARYL-N-BOC (OR N-FMOC) OXAZIRIDINES [J].

VIDAL, J ;

DAMESTOY, S ;

COLLET, A .

TETRAHEDRON LETTERS, 1995, 36 (09) :1439-1442

[13] N-AMINATION USING N-METHOXYCARBONYL-3-PHENYLOXAZIRIDINE - DIRECT ACCESS TO CHIRAL N-BETA-PROTECTED ALPHA-HYDRAZINO ACIDS AND CARBAZATES [J].

VIDAL, J ;

DROUIN, J ;

COLLET, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) :435-437

[14] ELECTROPHILIC AMINATION - PREPARATION AND USE OF N-BOC-3-(4-CYANOPHENYL)OXAZIRIDINE, A NEW REAGENT THAT TRANSFERS A N-BOC GROUP TO N-NUCLEOPHILES AND C-NUCLEOPHILES [J].

VIDAL, J ;

GUY, L ;

STERIN, S ;

COLLET, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4791-4793

[15]

Xiao XY, 1997, J ORG CHEM, V62, P6968

← 1 2 →