Highly regio- and diastereoselective palladium-catalyzed allylic substitution. Synthesis of 3-(2-aminobutylidene)-4-arylazetidin-2-ones

被引：10

作者：

Cardillo, G ^{[1
]}

Fabbroni, S ^{[1
]}

Gentilucci, L ^{[1
]}

Perciaccante, R ^{[1
]}

Tolomelli, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 06期

关键词：

allylic substitution; azetidinone; diastereoselectivity; palladium; regioselectivity;

D O I：

10.1002/adsc.200404385

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The palladium-catalyzed benzylamine attack to a particular allylic moiety, the 3-alkenyl-3-bromoazetidin-2-one is herein reported. This reaction shows interesting mechanistic aspects and allows us to introduce in one step and under high regio- and stereocontrol the amino function in the C3 side chain of non-conventional beta-lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.

引用

收藏

页码：833 / 838

页数：6

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