title: Asymmetric vinylogous Michael reaction of alpha,beta-unsaturated ketones with gamma-butenolide under multifunctional catalysis.
abstract: 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).
authors.affiliation: 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.
authors.forename: Huicai
authors.initials: H
authors.lastname: Huang
authors.forename: Feng
authors.initials: F
authors.lastname: Yu
authors.forename: Zhichao
authors.initials: Z
authors.lastname: Jin
authors.forename: Wenjun
authors.initials: W
authors.lastname: Li
authors.forename: Wenbin
authors.initials: W
authors.lastname: Wu
authors.forename: Xinmiao
authors.initials: X
authors.lastname: Liang
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
mesh_terms: 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
chemical_list: D000588:Amines; D007659:Ketones; C004511:butenolide; D015107:4-Butyrolactone