title: TBAF-Triggered Aldol-Type Addition of α-Triethylsilyl-α-diazoacetone.
abstract: Aldol-type addition of α-triethylsilyl-α-diazoacetone was achieved under nucleophilic activation by tetrabutylammonium fluoride (TBAF). The use of a semistoichiometric amount of TBAF (protocol P1) provided the corresponding β-hydroxy-α-diazoacetone as the sole product. Alternatively, the use of a catalytic amount of TBAF led to a mixture of β-hydroxy- and β-silyloxy-α-diazoacetone products, which was cleanly desilylated with Et3N·3HF (protocol P2). The weakly basic conditions employed tolerate a wide range of substrates and constitute a high-yielding, convenient complementary procedure to the low-temperature LDA-promoted aldol-type addition of diazoacetone.
authors.affiliation: Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS, Faculté des Sciences et Techniques, Université du Maine , 72085 Cedex 9 Le Mans, France.|Laboratoire de Chimie Appliquée, Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, 3038 Sfax, Tunisia.
authors.forename: Imen
authors.initials: I
authors.lastname: Abid
authors.affiliation: Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS, Faculté des Sciences et Techniques, Université du Maine , 72085 Cedex 9 Le Mans, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Gosselin
authors.affiliation: Laboratoire CEISAM, UMR 6230 CNRS, Faculté des Sciences et des Techniques, Université de Nantes , 44322 Cedex 3 Nantes, France.
authors.forename: Monique
authors.initials: M
authors.lastname: Mathé-Allainmat
authors.affiliation: Laboratoire de Chimie Appliquée, Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, 3038 Sfax, Tunisia.
authors.forename: Souhir
authors.initials: S
authors.lastname: Abid
authors.affiliation: Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS, Faculté des Sciences et Techniques, Université du Maine , 72085 Cedex 9 Le Mans, France.
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin
authors.affiliation: Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS, Faculté des Sciences et Techniques, Université du Maine , 72085 Cedex 9 Le Mans, France.
authors.forename: Catherine
authors.initials: C
authors.lastname: Gaulon-Nourry
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001391:Azo Compounds; D017646:Organosilicon Compounds; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium