Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine.
An asymmetric direct aldol reaction of acetoacetals is described. Under the catalysis of a simple chiral primary amine, the direct aldol reactions of acetoacetals occur exclusively on the gamma-position to give vinylogous-type aldol products with high diastereo- and enantioselectivity.
Luo
Sanzhong
S
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. luosz@iccas.ac.cn
Qiao
Yupu
Y
Zhang
Long
L
Li
Jiuyuan
J
Li
Xin
X
Cheng
Jin-Pei
JP
D000080:Acetals / Q000737:chemistry*; D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000080:Acetals; D000085:Acetates; D000447:Aldehydes; D000588:Amines; D001688:Biological Products; D007659:Ketones; D018942:Macrolides; D012997:Solvents; D014753:Vinyl Compounds; C116609:3-hydroxybutanal