Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system.: Synthesis of 3-Alkenyl-Δ3-cephems

被引：6
|
作者：
Tanaka, H [1 ]
Zhao, JF [1 ]
Kumase, H [1 ]
机构：
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 02期
关键词：
D O I：
10.1021/jo001429b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of 3-alkenyl-Delta (3)-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Delta (3)-cephem with alkenyl halides, e.g., vinyl bromide, trans-1-bromo-1-propene, and trans-beta -bromostyrene in an Al/cat . PbBr2/cat . NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Delta (3)-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.
引用
收藏
页码：570 / 577
页数：8
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