title: Highly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2.
abstract: The diastereospecific formation of δ-hydroxyalkylbutenolide phosphonate has been achieved via a vinylogous Mukaiyama aldol reaction. The reaction was performed using α-ketophosphonate 1 and 2-(trimethylsilyloxy)furan 2 mediated by Cu(OTf)(2) and 2,2,2-trifluoroethanol as additive in CH(2)Cl(2). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-one phosphonates 3 in high yields with good to excellent diastereoselectivities (d.r. up to >99 : 1). 5-(Hydroxy(alkyl)methyl)furan-2(5H)-one phosphonates could also be obtained with good diastereoselectivities.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.
authors.forename: Jipan
authors.initials: J
authors.lastname: Yu
authors.forename: Xiaona
authors.initials: X
authors.lastname: Zhao
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Miao
authors.forename: Ruyu
authors.initials: R
authors.lastname: Chen
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014270:Trifluoroethanol / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D005663:Furans; D007659:Ketones; D008698:Mesylates; D063065:Organophosphonates; D014297:Trimethylsilyl Compounds; D014270:Trifluoroethanol; C012077:trifluoromethanesulfonic acid