β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

被引：28

作者：

Clayden, J

Watson, DW

Helliwell, M

Chambers, M

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Merck Sharp & Dohme Res Labs, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 20期

关键词：

D O I：

10.1039/b308029c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substituted acrylamide derivatives of benzylamine are lithiated alpha to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a beta-electron withdrawing group, 4-exo-trig cyclisation to a beta-lactam.

引用

收藏

页码：2582 / 2583

页数：2

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