title: Highly enantio- and diastereoselective vinylogous aldol reaction by LiCl-assisted BINOL-titanium species.
abstract: The first highly enantio- and diastereoselective vinylogous aldol reaction between propionyl acetate-derived Brassard's diene and aldehydes was accomplished by titanium-lithium combined Lewis acid, affording δ-hydroxy-γ-methyl-β-methoxy acrylates. This methodology was utilized in convenient and concise construction of the polypropionate moiety in cystothiazole A and melithiazole C.
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Faculty of Chemical, Environmental and Biological Science and Technology, Dalian University of Technology, Dalian 116023, P. R. China.
authors.forename: Guowei
authors.initials: G
authors.lastname: Wang
authors.forename: Baomin
authors.initials: B
authors.lastname: Wang
authors.forename: Shuai
authors.initials: S
authors.lastname: Qi
authors.forename: Jinfeng
authors.initials: J
authors.lastname: Zhao
authors.forename: Yuhan
authors.initials: Y
authors.lastname: Zhou
authors.forename: Jingping
authors.initials: J
authors.lastname: Qu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D018021:Lithium Chloride / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry; D014025:Titanium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; C406944:BINOL, naphthol; D009284:Naphthols; D013844:Thiazoles; C112182:cystothiazole A; C116609:3-hydroxybutanal; D014025:Titanium; D018021:Lithium Chloride