A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides

被引：10
作者：
de Carne-Carnavalet, Benoit [1 ]
Meyer, Christophe [1 ]
Cossy, Janine [1 ]
Folleas, Benoit [2 ]
Brayer, Jean-Louis [2 ]
Demoute, Jean-Pierre [2 ]
机构：
[1] ESPCI ParisTech, CNRS, Chim Organ Lab, UMR7084, F-75231 Paris 05, France
[2] DiverChim, ZAC Moulin, F-95700 Roissy En France, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期
关键词：
CHIRAL BASE DESYMMETRISATION; N-ACYLIMINIUM IONS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; INDOLE-DERIVATIVES; TERMINAL ALKYNES; RING-SYSTEM; IMIDES; ACID;
D O I：
10.1021/jo400713u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropane-carboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.
引用
收藏
页码：5794 / 5799
页数：6
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