title: Highly enantio- and diastereoselective synthesis of β-methyl-γ-monofluoromethyl-substituted alcohols.
abstract: Enanatiopure β-methyl-γ-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl)methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)(2)AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, PR China.
authors.forename: Wenguo
authors.initials: W
authors.lastname: Yang
authors.forename: Xinle
authors.initials: X
authors.lastname: Wei
authors.forename: Yuanhang
authors.initials: Y
authors.lastname: Pan
authors.forename: Richmond
authors.initials: R
authors.lastname: Lee
authors.forename: Bo
authors.initials: B
authors.lastname: Zhu
authors.forename: Hongjun
authors.initials: H
authors.lastname: Liu
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Kuo-Wei
authors.initials: KW
authors.lastname: Huang
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000438:Alcohols; D002254:Carbonates; D002930:Cinchona Alkaloids; D006845:Hydrocarbons, Fluorinated; D013450:Sulfones; C517722:bis(phenylsulfonyl)methane; C546375:fluorobis(phenylsulfonyl)methane; D008697:Methane