anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst.
A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the alpha-imino ester 4 proceed smoothly to give the functional beta-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible.
Kano
Taichi
T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Yamaguchi
Yukako
Y
Tokuda
Osamu
O
Maruoka
Keiji
K
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000447:Aldehydes; D006576:Heterocyclic Compounds, 4 or More Rings; D008352:Mannich Bases; D013449:Sulfonamides; C032251:isovalerylaldehyde