title: Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones.
abstract: Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
authors.forename: Guo-Gui
authors.initials: GG
authors.lastname: Liu
authors.forename: Mei-Qiu
authors.initials: MQ
authors.lastname: Li
authors.forename: Yong
authors.initials: Y
authors.lastname: Zhang
authors.forename: Shao-Yun
authors.initials: SY
authors.lastname: Zhang
authors.forename: Jun-Ru
authors.initials: JR
authors.lastname: Qiu
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Xu
authors.forename: Shun-Jun
authors.initials: SJ
authors.lastname: Ji
authors.forename: Xing-Wang
authors.initials: XW
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D002930:Cinchona Alkaloids; D003512:Cyclohexanones; D009574:Nitro Compounds; D009595:Nitroparaffins; D013890:Thiourea; D008697:Methane; C008640:nitromethane