First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates.
Chiral amines catalyze the enantioselective conjugate addition of aldehydes to vinyl phosphonates in high yields and with enantioselectivities up to 97% ee. This novel process provides synthetically useful chiral gamma-geminal phosphonate aldehydes which can be easily converted in a few steps into chiral beta-substituted vinyl phosphonates with conservation of the optical purity.
Sulzer-Mossé
Sarah
S
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.
Tissot
Matthieu
M
Alexakis
Alexandre
A
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D048289:Imidazolidines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000447:Aldehydes; D048289:Imidazolidines; D063065:Organophosphonates; D014753:Vinyl Compounds