title: Enantioselective and regioselective organocatalytic conjugate addition of malonates to nitroenynes.
abstract: The first catalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroenynes catalyzed by cinchona alkaloid-based thiourea organocatalysts has been developed. The 1,4-addition adducts were obtained solely, in moderate to good yields (up to 93%) with good enantioselectivities (up to 99% ee). This protocol affords a conceptually different entry to the precursors of pharmaceutically important chiral β-alkynyl acid derivatives and synthetically useful chiral nitroalkynes. Notably, the protocol worked well with both aryl- and alkyl-substituted alkynyl substrates.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 China.
authors.forename: Xiao-Jiao
authors.initials: XJ
authors.lastname: Li
authors.forename: Fang-Zhi
authors.initials: FZ
authors.lastname: Peng
authors.forename: Xiang
authors.initials: X
authors.lastname: Li
authors.forename: Wen-Tao
authors.initials: WT
authors.lastname: Wu
authors.forename: Zhong-Wen
authors.initials: ZW
authors.lastname: Sun
authors.forename: Ying-Mei
authors.initials: YM
authors.lastname: Li
authors.forename: Shao-Xiong
authors.initials: SX
authors.lastname: Zhang
authors.forename: Zhi-Hui
authors.initials: ZH
authors.lastname: Shao
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002930:Cinchona Alkaloids; D008314:Malonates; D013890:Thiourea