The synthesis of functionalised β- and γ-lactams by cyclisation of enamides using copper(I) or ruthenium(II)

被引：39
作者：
Bryans, JS
Chessum, NEA
Parsons, AF [1 ]
Ghelfi, F
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] Pfizer Global Res & Dev, Cambridge CB2 2QB, England
[3] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 15期
基金：
英国生物技术与生命科学研究理事会;
关键词：
copper and compounds; lactams; radicals and radical reactions; ruthenium and compounds;
D O I：
10.1016/S0040-4039(01)00320-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclisation of a variety of halo-enamides with copper(I) or ruthenium(II) complexes has been investigated. The regioselectivity of the radical cyclisation, which can proceed via either a 4-exo or 5-endo pathway, to form beta- or gamma -lactam products respectively, is determined by the nature of the metal oxidant and the reaction conditions. Thus, whereas copper(I)bipyridine reactions give predominantly gamma -lactams, the use of copper(I)/TMEDA or dichlorotris(triphenylphosphine)ruthenium(II) affords mainly beta -lactams. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码：2901 / 2905
页数：5
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