Enantioselective synthesis of beta-amino esters and its application to the synthesis of the enantiomers of the antidepressant Venlafaxine.
Beta-amino esters are readily formed from the rhodium(II) prolinate-catalyzed intermolecular C-H insertion between methyl aryldiazoacetates and a bis-silyl protected methylamine.
Davies
Huw M L
HM
Department of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260-3000, USA. hdavies@buffalo.edu
Ni
Aiwu
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D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry; D018687:Antidepressive Agents, Second-Generation / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D008744:Methylamines / Q000737:chemistry; D011392:Proline / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D000069470:Venlafaxine Hydrochloride
D000588:Amines; D000596:Amino Acids; D000700:Analgesics; D018687:Antidepressive Agents, Second-Generation; D003511:Cyclohexanols; D003979:Diazonium Compounds; D004952:Esters; D008744:Methylamines; D000069470:Venlafaxine Hydrochloride; D011392:Proline; C027451:methylamine; D012238:Rhodium