2H-Azirine 3-phosphonates: a new class of chiral iminodienophiles. Asymmetric synthesis of quaternary piperidine phosphonates.
[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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
Wu
Yongzhong
Y
Yan
Hongxing
H
Prasad
Kavirayani R
KR
McCoull
William
W
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
D001389:Azirines; D007202:Indicators and Reagents; D063065:Organophosphonates; D010880:Piperidines