title: Enantioselective electrophilic trifluoromethylation of beta-keto esters with Umemoto reagents induced by chiral nonracemic guanidines.
abstract: Chiral nonracemic guanidines act as Brønsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of beta-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60-70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination of chemists to design new chiral bases to improve the stereochemical outcome.
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Shun
authors.initials: S
authors.lastname: Noritake
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Nomura
authors.forename: Yiyong
authors.initials: Y
authors.lastname: Huang
authors.forename: Andrej
authors.initials: A
authors.lastname: Matsnev
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Takeshi
authors.initials: T
authors.lastname: Toru
authors.forename: Dominique
authors.initials: D
authors.lastname: Cahard
mesh_terms: D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008745:Methylation; D013237:Stereoisomerism
chemical_list: D005617:Chlorofluorocarbons, Methane; D004952:Esters; D006146:Guanidines; D007202:Indicators and Reagents; C009554:fluoroform