An easy approach to optically active alpha-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates.
A catalytic direct enantioselective electrophilic amination of beta-keto phosphonates has been developed applying chiral bisoxazoline-zinc(II) complexes as the catalyst. The reaction proceeds well for both acyclic and cyclic substrates in high yields and with up to 98% ee using azodicarboxylates as the nitrogen source. The scope of the reaction is, for example, the further transformation to optically active beta-hydroxy-alpha-amino phosphonates with very high stereoselection.
Bernardi
Luca
L
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Zhuang
Wei
W
Jørgensen
Karl Anker
KA
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003998:Dicarboxylic Acids / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000596:Amino Acids; D001391:Azo Compounds; D003998:Dicarboxylic Acids; D007659:Ketones; D063065:Organophosphonates; D023303:Oxazolidinones; D015032:Zinc