The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction.
An efficient direct aldol reaction has been developed for the synthesis of chiral beta-hydroxy ketone using a combination of C(1)-symmetric chiral prolinamides based on o-phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts.
Lu
Zhijin
Z
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Mei
Haibo
H
Han
Jianlin
J
Pan
Yi
Y
D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D010655:Phenylenediamines / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D001547:Benzaldehydes; D003512:Cyclohexanones; D007659:Ketones; D008698:Mesylates; D010655:Phenylenediamines; C029915:4-nitrobenzaldehyde; C036468:cyclohexanone; C034193:1,2-diaminobenzene; D011392:Proline; D005634:Fructose-Bisphosphate Aldolase; C012077:trifluoromethanesulfonic acid; C056291:prolinamide