title: Diastereoselective and enantioselective capture of chiral zinc enolate using nitroolefins: a rapid access to chiral γ-nitro carbonyl compounds.
abstract: Highly diastereoselective and enantioselective catalytic capture of chiral zinc enolates using nitroolefins as electrophiles is described. The tandem products γ-nitro ketones were obtained in good yields with high diastereoselectivities and enantioselectivities. The γ-nitro ketones were readily hydrogenated to the optically enriched and diastereomerically pure chiral pyrrolidines with four contiguous stereocentres under mild conditions.
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, Nanchong, P R China.
authors.forename: Cheng-Yan
authors.initials: CY
authors.lastname: Ni
authors.forename: Sha-Sha
authors.initials: SS
authors.lastname: Kan
authors.forename: Quan-Zhong
authors.initials: QZ
authors.lastname: Liu
authors.forename: Tai-Ran
authors.initials: TR
authors.lastname: Kang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D008958:Models, Molecular; D009574:Nitro Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000475:Alkenes; D009574:Nitro Compounds; D011759:Pyrrolidines; D015032:Zinc