title: Highly enantioselective direct syn- and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts.
abstract: 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.
authors.affiliation: 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
authors.forename: Sanzhong
authors.initials: S
authors.lastname: Luo
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
authors.forename: Long
authors.initials: L
authors.lastname: Zhang
authors.forename: Jiuyuan
authors.initials: J
authors.lastname: Li
authors.forename: Jin-Pei
authors.initials: JP
authors.lastname: Cheng
mesh_terms: D000446:Aldehyde-Lyases / Q000378:metabolism*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004098:Dihydroxyacetone / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; C116609:3-hydroxybutanal; D000446:Aldehyde-Lyases; D004098:Dihydroxyacetone