title: Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (-)-galanthamine.
abstract: A Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO has been developed to synthesize functionalized 2-methylidene-3,4-cyclohexenones. The scope of this methodology has been investigated, showing that various functional groups can be tolerated. Both di- and tri-substituted allenylcyclopropanes can be applied to this cycloaddition and the [5 + 1] cycloadducts with the E configuration were obtained as the major products. In addition, the present [5 + 1] cycloaddition reaction has been utilized as a key step in the formal synthesis of the natural product (-)-galanthamine.
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China. yuzx@pku.edu.cn.
authors.forename: Cheng-Hang
authors.initials: CH
authors.lastname: Liu
authors.forename: Zhi-Xiang
authors.initials: ZX
authors.lastname: Yu
mesh_terms: D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D005702:Galantamine; D002248:Carbon Monoxide; C030797:cyclopropane; D012238:Rhodium