title: Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones.
abstract: An unprecedented domino synthesis of tetrahydrobenzofuran-4-ones is described implicating chemoselective alkylation of various 1,3-cyclohexanediones with bromocrotonate or crotonitrile followed by oxa-Michael cyclization. Further transformations of this core to reach molecular diversity are also presented.
authors.affiliation: Laboratoire des Fonctions Azotées et Oxygénées Complexes de l'IRCOF, CNRS UMR 6014 & FR 3038, Université de Rouen, Mont Saint-Aignan, 76130, France.
authors.forename: Rema B
authors.initials: RB
authors.lastname: Devi
authors.forename: Matthias
authors.initials: M
authors.lastname: Henrot
authors.forename: Michaël
authors.initials: M
authors.lastname: De Paolis
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
mesh_terms: D000478:Alkylation; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D003437:Crotonates / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D003437:Crotonates; D003512:Cyclohexanones; D009570:Nitriles; C008110:3,3'-iminodipropionitrile; C004636:1,3-cyclohexanedione