Proline-catalyzed, asymmetric mannich reactions in the synthesis of a DPP-IV inhibitor.
[reaction: see text] A highly stereoselective L-proline-catalyzed, asymmetric direct Mannich reaction between a glyoxalate-derived imine and phenyl acetaldehyde was employed for the formation of a syn substituted beta-phenyl homoserine. This Mannich adduct was then readily elaborated to a functionalized beta-phenyl aspartic acid derivative through a series of mild and efficient transformations.
Janey
Jacob M
JM
Department of Process Research, Merck Research Laboratories, Merck and Co., Inc., Rahway, New Jersey 07065, USA. jacob_janey@merck.com
Hsiao
Yi
Y
Armstrong
Joseph D
JD
D000447:Aldehydes / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002384:Catalysis; D018819:Dipeptidyl Peptidase 4 / Q000378:metabolism*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000447:Aldehydes; D000605:Amino Alcohols; D011480:Protease Inhibitors; D011392:Proline; D018819:Dipeptidyl Peptidase 4