title: Organocatalytic asymmetric synthesis of 1,1-diarylethanes by transfer hydrogenation.
abstract: A new organocatalytic transfer hydrogenation strategy for the asymmetric synthesis of 1,1-diarylethanes is described. Under mild conditions, a range of 1,1-diarylethanes substituted with an o-hydroxyphenyl or indole unit could be obtained with excellent efficiency and enantioselectivity. We also extended the protocol to an unprecedented asymmetric hydroarylation of 1,1-diarylalkenes with indoles for the synthesis of a range of highly enantioenriched 1,1,1-triarylethanes bearing acyclic all-carbon quaternary stereocenters. These diaryl- and triarylethanes exhibit impressive cytotoxicity against a number of human cancer cell lines. Preliminary mechanistic studies combined with DFT calculations provided important insight into the reaction mechanism.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong SAR, China.
authors.forename: Zhaobin
authors.initials: Z
authors.lastname: Wang
authors.forename: Fujin
authors.initials: F
authors.lastname: Ai
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Wanxiang
authors.initials: W
authors.lastname: Zhao
authors.forename: Guangyu
authors.initials: G
authors.lastname: Zhu
authors.forename: Zhenyang
authors.initials: Z
authors.lastname: Lin
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
mesh_terms: D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004980:Ethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D006865:Hydrogenation; D061986:MCF-7 Cells; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D009943:Organophosphorus Compounds; D011725:Pyridines; D004980:Ethane