title: New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade reaction catalyzed by chiral diamine-Ni(OAc)2 complex.
abstract: A highly efficient catalyst system assembled from enantiomerically pure diaminocyclohexane and Ni(OAc)(2) is, for the first time, used to catalyze the cascade Michael-Henry reaction of various diones and substituted nitroalkenes. A series of polyfunctionalized bicyclo[3.2.1]octane derivatives containing four stereogenic centers are prepared with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to 50 : 1 dr) with high yields. In addition, via this chiral diamine-Ni(OAc)(2) catalyst system, the base-induced epimerization leading to the decrease of stereoselectivity can be prevented.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science, Lanzhou University, Lanzhou 730000, China.
authors.forename: Wenyi
authors.initials: W
authors.lastname: Li
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Liu
authors.forename: Zhifeng
authors.initials: Z
authors.lastname: Mao
authors.forename: Qiao
authors.initials: Q
authors.lastname: Chen
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D001688:Biological Products / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009795:Octanes / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D003959:Diamines; D009795:Octanes; D009942:Organometallic Compounds; C574915:diamine-Ni(OAc)2; C026728:octane