title: Cinchona-based primary amine-catalyzed asymmetric cascade aza-Michael-aldol reactions of enones with 2-(1H-pyrrol-2-yl)-2-oxoacetates: synthesis of chiral pyrrolizines with multistereocenters.
abstract: Cinchona-based primary amine-catalyzed cascade aza-Michael-aldol reactions of α,β-unsaturated ketones with 2-(1H-pyrrol-2-yl)-2-oxoacetates provided highly functionalized chiral pyrrolizines bearing multistereocenters including a chiral quaternary carbon center in good yields (up to 92%) with excellent levels of stereocontrol (90-95% ee, >20:1 dr in all cases). The ketone group in the cascade product was asymmetrically reduced to chiral secondary hydroxyl groups in good yields.
authors: Department of Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea.
authors: Hyo-Jun
authors: HJ
authors: Lee
authors: Chang-Woo
authors: CW
authors: Cho
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry*; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D062385:Hydroxybenzoates; D007659:Ketones; D011758:Pyrroles