Catalytic asymmetric synthesis of α,β-disubstituted α,γ-diaminophosphonic acid precursors by Michael addition of α-substituted nitrophosphonates to nitroolefins.
Michael additions of α-substituted nitrophosphonates to various nitroolefins are shown to proceed with high diastereo- and enantioselectivity when catalyzed by a quinine-derived thiourea-tertiary amine bifunctional catalyst and generate α,γ-diaminophosphonic acid precursors with contiguous quaternary and tertiary stereocenters.
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, India.
Chandra Bhushan
CB
Tripathi
Satavisha
S
Kayal
Santanu
S
Mukherjee
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D009574:Nitro Compounds; D063065:Organophosphonates