Enantioselective synthesis of quaternary α-aminophosphonates via conjugate addition of α-nitrophosphonates to enones.
Enantioselective Michael addition of α-nitrophosphonates to enones for the synthesis of α-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary α-aminophosphonates via in situ reduction-intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction-intramolecular cyclization.
Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
Kalisankar
K
Bera
Irishi N N
IN
Namboothiri
D000473:Alkanes / Q000737:chemistry*; D000586:Amination; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000473:Alkanes; D007659:Ketones; D017672:Nitrogen Compounds; D063065:Organophosphonates