title: Organocatalytic and highly stereoselective direct vinylogous Mannich reaction.
abstract: The first direct asymmetric vinylogous Mannich (AVM) reaction of alpha,alpha-dicyanoolefins and N-Boc aldimines was described promoted by a simple chiral bifunctional thiourea-tertairy amine organocatalyst. The reaction was highly efficient (S/C up to 1000) and regio-, stereoselective (generally >99% de, 96 to >99.5% ee) at room temperature for a broad array of substrates. Enantiomerically pure delta-amino acid could be smoothly prepared from the adduct.
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Tian-Yu
authors.initials: TY
authors.lastname: Liu
authors.forename: Hai-Lei
authors.initials: HL
authors.lastname: Cui
authors.forename: Jun
authors.initials: J
authors.lastname: Long
authors.forename: Bang-Jing
authors.initials: BJ
authors.lastname: Li
authors.forename: Yong
authors.initials: Y
authors.lastname: Wu
authors.forename: Li-Sheng
authors.initials: LS
authors.lastname: Ding
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D000596:Amino Acids; D009570:Nitriles; D014753:Vinyl Compounds; D013890:Thiourea