Enantioselective assembly of substituted dihydropyrones via organocatalytic reaction in water media.
The diarylprolinol ether/HOAc-catalyzed cascade Michael addition and cyclization of aldehydes and alpha-keto-alpha,beta-unsaturated esters proceeds smoothly in water to afford cyclic hemiacetals, which are oxidized to furnish highly functionalized 3,4,5,6-tetrasubstituted dihydropyrones with excellent enantioselectivities.
Wang
Jing
J
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.
Yu
Fang
F
Zhang
Xiaojing
X
Ma
Dawei
D
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water
D000447:Aldehydes; D004952:Esters; D011753:Pyrones; D014867:Water