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
Baldovini, N
Bertrand, MP
Carriere, A
Nouguier, R
Plancher, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3205 - 3208
[2] Synthesis of heterocycles by radical cyclisation
Bowman, WR
Bridge, CF
Brookes, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01): : 1 - 14
[3] Ligand geometry effects in copper mediated atom transfer radical cyclisations.
Clark, AJ
Filik, RP
Thomas, GH
[J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4885 - 4888
[4] Efficient room temperature copper(I) mediated 5-endo radical cyclisations
Clark, AJ
Dell, CP
Ellard, JM
Hunt, NA
McDonagh, JP
[J]. 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.
Clark, AJ
Duncalf, DJ
Filik, RP
Haddleton, DM
Thomas, GH
Wongtap, H
[J]. 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
Clark, AJ
De Campo, F
Deeth, RJ
Filik, RP
Gatard, S
Hunt, NA
Lastécouères, D
Thomas, GH
Verlhac, JB
Wongtap, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05): : 671 - 680
[7] Solid-supported catalysts for atom-transfer radical cyclization of 2-haloacetamides
Clark, AJ
Filik, RP
Haddleton, DM
Radigue, A
Sanders, CJ
Thomas, GH
Smith, ME
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8954 - 8957
[8] RECENT APPLICATIONS OF RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS
CURRAN, DP
SISKO, J
YESKE, PE
LIU, H
[J]. PURE AND APPLIED CHEMISTRY, 1993, 65 (06) : 1153 - 1159
[9] Copper(I) reactions in N-heterocycle synthesis:: efficient preparation of substituted pyrrolidinones
Davies, DT
Kapur, N
Parsons, AF
[J]. TETRAHEDRON LETTERS, 1999, 40 (49) : 8615 - 8618
[10] New and improved catalysts for transition metal catalysed radical reactions
de Campo, F
Lastécouères, D
Verlhac, JB
[J]. CHEMICAL COMMUNICATIONS, 1998, (19) : 2117 - 2118

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