Efficient β-lactam synthesis via 4-exo atom transfer radical cyclisation using CuBr(tripyridylamine) complex

被引：35

作者：

Clark, AJ ^{[1
]}

Battle, GM

Bridge, A

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

[2] Aventis Pharma Ltd, Dagenham RM10 7XS, Essex, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

radicals and radical reactions; cyclisations; copper and compounds;

D O I：

10.1016/S0040-4039(01)00737-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tripyridylamine cogper(I) halide complex mediates the atom transfer radical cyclisation of bromo-enamides to give beta -lactams exclusively with no formation of gamma -lactams. Initial products 7 arise from 4-exo bromine atom transfer but elimination can be readily achieved by reaction with DBU to furnish alkenes 8 in high yields (92-98%). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4409 / 4412

页数：4

共 30 条

[1] 3-oxa- and 3-azabicyclo[3.1.0]hexan-2-ones via tandem radical cyclization-intramolecular S(N)2 reactions [J].

Baldovini, N ;

Bertrand, MP ;

Carriere, A ;

Nouguier, R ;

Plancher, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3205-3208

[2] Synthesis of heterocycles by radical cyclisation [J].

Bowman, WR ;

Bridge, CF ;

Brookes, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01) :1-14

[3] Ligand geometry effects in copper mediated atom transfer radical cyclisations. [J].

Clark, AJ ;

Filik, RP ;

Thomas, GH .

TETRAHEDRON LETTERS, 1999, 40 (26) :4885-4888

[4] Efficient room temperature copper(I) mediated 5-endo radical cyclisations [J].

Clark, AJ ;

Dell, CP ;

Ellard, JM ;

Hunt, NA ;

McDonagh, JP .

TETRAHEDRON LETTERS, 1999, 40 (49) :8619-8623

[5] N-alkyl-2-pyridylmethanimines as tuneable alternatives to bipyridine ligands in copper mediated atom transfer radical cyclisation. [J].

Clark, AJ ;

Duncalf, DJ ;

Filik, RP ;

Haddleton, DM ;

Thomas, GH ;

Wongtap, H .

TETRAHEDRON LETTERS, 1999, 40 (19) :3807-3810

[6] Atom transfer radical cyclisations of activated and unactivated N-allylhaloacetamides and N-homoallylhaloacetamides using chiral and non-chiral copper complexes [J].

Clark, AJ ;

De Campo, F ;

Deeth, RJ ;

Filik, RP ;

Gatard, S ;

Hunt, NA ;

Lastécouères, D ;

Thomas, GH ;

Verlhac, JB ;

Wongtap, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :671-680

[7] Solid-supported catalysts for atom-transfer radical cyclization of 2-haloacetamides [J].

Clark, AJ ;

Filik, RP ;

Haddleton, DM ;

Radigue, A ;

Sanders, CJ ;

Thomas, GH ;

Smith, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8954-8957

[8] RECENT APPLICATIONS OF RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].

CURRAN, DP ;

SISKO, J ;

YESKE, PE ;

LIU, H .

PURE AND APPLIED CHEMISTRY, 1993, 65 (06) :1153-1159

[9] Copper(I) reactions in N-heterocycle synthesis:: efficient preparation of substituted pyrrolidinones [J].

Davies, DT ;

Kapur, N ;

Parsons, AF .

TETRAHEDRON LETTERS, 1999, 40 (49) :8615-8618

[10] New and improved catalysts for transition metal catalysed radical reactions [J].

de Campo, F ;

Lastécouères, D ;

Verlhac, JB .

CHEMICAL COMMUNICATIONS, 1998, (19) :2117-2118

← 1 2 3 →