Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.
A new class of organocatalysts has been designed by rational combination of proline with cinchona alkaloids. The chiral amine 3a, prepared from l-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes (up to 98% ee). The cinchonidine backbone is essential to the reaction efficiency and enantioselectivity.
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Jia-Rong
JR
Chen
Xiao-Lei
XL
An
Xiao-Yu
XY
Zhu
Xu-Fan
XF
Wang
Wen-Jing
WJ
Xiao
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D007659:Ketones; D009578:Nitrobenzenes; C116609:3-hydroxybutanal; C036077:nitrobenzene