Sequential combination of Michael and acetalization reactions: direct catalytic asymmetric synthesis of functionalized 4-nitromethyl-chromans as drug intermediates.
Functionalized chiral 4-nitromethyl-chromans as drug intermediates were achieved for the first time through sequential combination of Michael and acetalization reactions on 2-(2-nitro-vinyl)-phenols with acetone and alcohols in the presence of a catalytic amount of 9-amino-9-deoxyepiquinine and Ph(2)CHCO(2)H followed by p-TSA.
Ramachary
Dhevalapally B
DB
School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India. ramsc@uohyd.ernet.in
Sakthidevi
Rajasekar
R
D000096:Acetone / Q000138:chemical synthesis / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D002839:Chromans; D004364:Pharmaceutical Preparations; D010636:Phenols; D000096:Acetone; C051224:methyl radical; D009584:Nitrogen; D008697:Methane