title: 2H-Azirine 3-phosphonates: a new class of chiral iminodienophiles. Asymmetric synthesis of quaternary piperidine phosphonates.
abstract: [reaction: see text] Diels-Alder reactions of enantiomerically enriched 2H-azirine 3-phosphonates and dienes stereoselectively furnish optically pure, bicyclic aziridine adducts that on hydrogenation afford the first examples of enantiopure quaternary piperidine phosphonates.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Yongzhong
authors.initials: Y
authors.lastname: Wu
authors.forename: Hongxing
authors.initials: H
authors.lastname: Yan
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
authors.forename: William
authors.initials: W
authors.lastname: McCoull
mesh_terms: D001389:Azirines / Q000737:chemistry*; D003500:Cyclization; D006865:Hydrogenation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001389:Azirines; D007202:Indicators and Reagents; D063065:Organophosphonates; D010880:Piperidines