Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.
A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios.
Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.
Marcus
M
Blümel
Pankaj
P
Chauhan
Robert
R
Hahn
Gerhard
G
Raabe
Dieter
D
Enders
D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry
D003503:Cyclobutanes; D011725:Pyridines; D013449:Sulfonamides; C527748:squaric acid amide; D011803:Quinine