174710-92-0Relevant academic research and scientific papers
Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification
Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 116 - 120 (2018/12/05)
An asymmetric cyanation of acylsilanes involving the in-situ formation of chiral acylsilane cyanohydrins followed by their kinetic resolution via organocatalytic cycloetherification is described. The highly enantio- and diastereoselective cycloetherificat
Chemistry of silyl thioketones part 9. 1 A new selective synthesis of 1-silyl-1-enethiols and of 2-silyl-thiacycloalk-2-enes of common to large ring size
Bonini, Bianca F.,Comes-Franchini, Mauro,Fochi, Mariafrancesca,Mazzanti, Germana,Ricci, Alfredo
, p. 4803 - 4816 (2007/10/03)
ω-Haloacylsilanes 1 were selectively transformed via thioacylsilanes into Z-silyl-enethiols 4 with solid sodium hydrogen carbonate or into 2-silylthiacycloalk-2-enes5 of common to large ring size with solid sodium hydroxide. Compounds 5 underwent protiode
Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride
Chuang, Tsung-Hsun,Fang, Jim-Min,Jiaang, Weir-Torn,Tsai, Yeun-Min
, p. 1794 - 1805 (2007/10/03)
A series of acyl silanes including aliphatic-, aromatic-, and bis-acyl silanes, as well as the acyl silanes bearing other substituents such as a bromine atom and alkenyl, succinimide, and carbonyl groups, were prepared, and their reactions with samarium diiodide or tributylstannane were studied. The reactions of acyl silanes occurred in various manners such as reductions, reductive alkylations, intramolecular radical cyclizations, pinacol couplings, aldol reactions, and Tishchenko reactions, depending on the nature of substrates and reaction conditions. Acyl silanes were generally reduced to give the corresponding α-silyl alcohols without transfer of silyl groups. Intramolecular radical cyclizations of 5-hexenoyl silanes and 1-silyl-1,5-pentanedione were realized to give α-silyl cyclopentanols and 1,2-cyclopentanediol derivatives, respectively. On treatment with samarium diiodide in tetrahydrofuran, 1-(trimethylsilyl)-1,6-hexanedione underwent a pinacol coupling reaction in the presence of t-BuOH, whereas it underwent a Tishchenko reaction in the presence of MeOH. The Tishchenko reaction of 1-silyl-1,5-pentanedione gave a δ-silyl-δ-lactone. On treating with samarium diiodide, 1-(trimethylsilyl)-1,5-hexanedione and 1,5-bis(trimethylsilyl)-1,6-hexanedione, underwent, respectively, intramolecular aldol reactions.
