title: O-Monoacyltartaric acid catalyzed enantioselective conjugate addition of a boronic acid to dienones: application to the synthesis of optically active cyclopentenones.
abstract: Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda-Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic intermediate of the antitumor agent TEI-9826. The study shows that a diene additive such as 1,6-heptadiene or diallyl ether was essential for the RCM.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.
authors.forename: Masaharu
authors.initials: M
authors.lastname: Sugiura
authors.forename: Ryo
authors.initials: R
authors.lastname: Kinoshita
authors.forename: Makoto
authors.initials: M
authors.lastname: Nakajima
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011455:Prostaglandins A, Synthetic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D001897:Boronic Acids; D003517:Cyclopentanes; D011455:Prostaglandins A, Synthetic; C469647:TEI9826; D013644:Tartrates; C013905:cyclopentenone; C029768:tartaric acid