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

页码：5794 / 5799

页数：6

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