title: Enantioselective organocatalytic Friedel-Crafts alkylation reaction of indoles with 5-hydroxyfuran-2(5H)-one: access to chiral γ-lactones and γ-lactams via a Ugi 4-center 3-component reaction.
abstract: 5-Hydroxyfuran-2(5H)-one 1, a readily available renewable resource, was used as an electrophile in the Friedel-Crafts alkylation of indoles catalyzed by a diphenylprolinol silyl ether. Moderate catalyst loading was achieved because of the high reactivity of 5-hydroxyfuran-2(5H)-one 1 in this process. Reduction of the Friedel-Crafts adduct (FC adduct) afforded indoyl lactones in high yield and enantioselectivity. Moreover, the FC adduct was used as a chiral synthon in a diversity-oriented synthesis, as illustrated by its successful engagement in a 4-center 3-component Ugi reaction (U-4C-3CR) to afford chiral five-membered lactams in high yield and enantioselectivity.
authors: Institut de Chimie Moléculaire de Reims, Université de Reims Champagne-Ardenne, CNRS UMR 6229, UFR Sciences Exactes et Naturelles, B.P. 1039 51687 Reims Cedex 2, France. emmanuel.riguet@univ-reims.fr
authors: Emmanuel
authors: E
authors: Riguet
mesh_terms: D000478:Alkylation; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002855:Chromatography, Thin Layer; D055808:Drug Discovery; D004987:Ethers / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D005663:Furans; D007211:Indoles; D007769:Lactams; D007783:Lactones; C529940:diphenylprolinol silyl ether; D011392:Proline