Highly enantioselective direct syn- and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts.
We present herein simple primary-tertiary diamine-Brønsted acid conjugates that catalyze both syn- and anti-aldol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities and enantioselectivities. This type of organocatalysts functionally mimics all four DHA aldolases, namely L-fuculose-1-phosphate aldolase, D-tagatose-1,6-diphosphate aldolase, D-fructose-1,6-diphosphate aldolase, and L-rhamnulose-1-phosphate aldolase.
Luo
Sanzhong
S
Beijing National Laboratory for Molecular Sciences (BNLMS), Center for Chemical Biology, Institute of Chemistry and Graduate School, Chinese Academy of Sciences, Beijing 100080, China. luosz@iccas.ac.cn
Xu
Hui
H
Zhang
Long
L
Li
Jiuyuan
J
Cheng
Jin-Pei
JP
D000446:Aldehyde-Lyases / Q000378:metabolism*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004098:Dihydroxyacetone / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; C116609:3-hydroxybutanal; D000446:Aldehyde-Lyases; D004098:Dihydroxyacetone