104011-57-6Relevant articles and documents
Asymmetric allylation with chiral formamide catalysts
Iseki, Katsuhiko,Mizuno, Shin,Kuroki, Yoshichika,Kobayashi, Yoshiro
, p. 977 - 988 (1999)
The successful example of chiral formamides that function as asymmetric catalysts is described. (S,S)-N,N-Bis(α-methylbenzyl)formamide mediates the enantioselective addition of allyl- and crotyltrichlorosilanes to aliphatic aldehydes with the assistance of hexamethylphosphoramide (HMPA) to afford the corresponding homoallylic alcohols in up to 98% enantiomeric excess.
Cp2TiCl2-Catalyzed Photoredox Allylation of Aldehydes with Visible Light
Bergamini, Giacomo,Calogero, Francesco,Cozzi, Pier Giorgio,Fermi, Andrea,Gualandi, Andrea,Guazzi, Simone,Mazzarini, Martino
, p. 3857 - 3863 (2020)
A Barbier-type Cp2TiCl2-mediated (10 mol %) photoredox allylation of aldehydes under irradiation with visible light (blue light-emitting diodes (LEDs), 450 nm) and in the presence of an organic dye (3DPAFIPN, 5 mol %) with allylbromides is described.
A chiral formamide: Design and application to catalytic asymmetric synthesis
Iseki, Katsuhiko,Mizuno, Shin,Kuroki, Yoshichika,Kobayashi, Yoshiro
, p. 2767 - 2770 (1998)
(S,S)-N,N-Bis(-α-methylbenzyl) formamide is the first example of chiral formamides that function as Lewis base catalysts to effectively serve catalytic asymmetric synthesis. The chiral formamide in combination with an additive, HMPA, catalyzes allylations
Lewis Acids Catalyze the Addition of Allylboronates to Aldehydes by Electrophilic Activation of the Dioxaborolane in a Closed Transition Structure
Rauniyar, Vivek,Hall, Dennis G.
, p. 4518 - 4519 (2004)
This study addressed the mechanism of the recently reported Lewis acid-catalyzed manifold for additions of allylboronates to aldehydes. A series of control experiments using various reagents and conditions, and kinetic studies by low-temperature NMR spectroscopy, were performed to investigate the origin of the activation provided by the best catalyst, Sc(OTf)3. The results obtained are strongly supportive of a mechanism involving electrophilic boron activation by coordination of the metal ion to one of the boronate oxygens in a closed bimolecular transition state. Copyright
Transition-metal-free reductive coupling of 1, 3-butadienes with aldehydes catalyzed by dibutyliodotin hydride
Suzuki, Itaru,Uji, Yuki,Kanaya, Shujiro,Ieki, Ryosuke,Tsunoi, Shinji,Shibata, Ikuya
supporting information, p. 5392 - 5394 (2017/11/07)
In this study, the Bu2SnIH-catalyzed direct coupling of 1, 3- dienes with aldehydes was developed. This reaction could be suitable for coupling without the use of transition-metal catalysts. Many types of aldehydes were applied to this reaction. The addition of MeOH promoted the catalytic cycle.
Direct, Mild, and General n-Bu4NBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides
Tekle-Smith, Makeda A.,Williamson, Kevin S.,Hughes, Isaac F.,Leighton, James L.
supporting information, p. 6024 - 6027 (2017/11/10)
A direct, mild, and general method for the enantioselective allylsilylation of aldehydes with allyl chlorides is reported. The reactions are effectively catalyzed by 5 mol % of n-Bu4NBr, and this rate acceleration allows the use of complex allyl donors in fragment-coupling reactions and of electron-deficient allyl donors. The results are (1) significant progress toward a "universal" asymmetric aldehyde allylation reaction that can reliably and highly stereoselectively couple any allyl chloride-aldehyde combination and (2) the discovery of a novel mode of nucleophilic catalysis for aldehyde allylsilylation reactions.
