Pengquan Chen, Chuanle Zhu, Rui Zhu, Zhiming Lin, Wanqing Wu and Huanfeng Jiang
Org. Biomol. Chem., 2017,15, 1228-1235
DOI:
10.1039/C6OB02137A,
Paper
A palladium-catalyzed cyclopropanation of internal alkenes with N-tosylhydrazones is presented. This gram-scale cyclopropanation reaction of maleimides provides a wide spectrum of 3-azabicyclo[3.1.0]hexane derivatives in high yields and diastereoselectivities. The major diastereoisomers could be easily isolated by chromatography on silica gel. This protocol provides a practical route to the mu opioid receptor antagonist CP-866,087.
![Graphical abstract: Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via palladium-catalyzed cyclopropanation of maleimides with N-tosylhydrazones: practical and facile access to CP-866,087](/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=C6OB02137A "Graphical abstract")
