Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivatives.
[reaction: see text] The first example of the Lewis acid-catalyzed three-component direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives is described. The procedure is highly atom economical and can be performed in a simple one-pot operation under mild conditions to afford a wide variety of synthetically important anti-alpha,beta-diamino ester derivatives in high yields with high diastereoselectivities.
Salter
Matthew M
MM
Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kobayashi
Jun
J
Shimizu
Yusuke
Y
Kobayashi
Shu
S
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005998:Glycine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D000596:Amino Acids; D004952:Esters; D005998:Glycine