title: Asymmetric decarboxylative 1,4-addition of malonic acid half thioesters to vinyl sulfones: highly enantioselective synthesis of 3-monofluoromethyl-3-arylpropanoic esters.
abstract: An asymmetric decarboxylative 1,4-addition of malonic acid half thioesters (MAHTs) to 2-aryl-substituted vinyl sulfones has been developed, yielding adducts with excellent enantioselectivity (up to 97 % ee). In view of tuning pKa values, a quinine-based benzyl-substituted thiourea was designed and demonstrated as the most efficient catalyst. The enantioselective synthesis of 3-monofluorinated analogues of 3-methyl indanone and (+)-turmerone has been accomplished from decarboxylative 1,4-addition adducts with satisfactory results.
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng, Henan, 475004 (P. R. China), Fax: (+86) 378-2864-665.
authors.forename: Baokun
authors.initials: B
authors.lastname: Qiao
authors.forename: Qian
authors.initials: Q
authors.lastname: Liu
authors.forename: Hongjun
authors.initials: H
authors.lastname: Liu
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D008314:Malonates; D011422:Propionates; D013450:Sulfones
keywords: asymmetric synthesis; decarboxylative 1,4-addition; monofluoromethylation; organocatalysis; vinyl sulfones