title: 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.
abstract: 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.
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Pengquan
authors.initials: P
authors.lastname: Chen
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Chuanle
authors.initials: C
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Zhiming
authors.initials: Z
authors.lastname: Lin
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Wanqing
authors.initials: W
authors.lastname: Wu
authors.affiliation: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. cewuwq@scut.edu.cn jianghf@scut.edu.cn.
authors.forename: Huanfeng
authors.identifier: http://orcid.org/0000-0002-4355-0294
authors.initials: H
authors.lastname: Jiang
mesh_terms: D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: C532932:3-azabicyclo(3.1.0)hexane; D053961:Azabicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; C000626492:CP-866,087; D003521:Cyclopropanes; D006586:Hexanes; D006835:Hydrazones; D008301:Maleimides; D014105:Tosyl Compounds; C043592:maleimide; D010165:Palladium