Asymmetric vinylogous Michael reaction of alpha,beta-unsaturated ketones with gamma-butenolide under multifunctional catalysis.
A general and direct organocatalytic asymmetric vinylogous Michael reaction of gamma-butenolide with alpha,beta-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile gamma-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30:1 dr and 95-99% ee).
Huang
Huicai
H
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Yu
Feng
F
Jin
Zhichao
Z
Li
Wenjun
W
Wu
Wenbin
W
Liang
Xinmiao
X
Ye
Jinxing
J
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000588:Amines; D007659:Ketones; C004511:butenolide; D015107:4-Butyrolactone