88761-82-4Relevant academic research and scientific papers
Asymmetric Conjugate Addition of Grignard Reagents to 3-Silyl Unsaturated Esters for the Facile Preparation of Enantioenriched β-Silylcarbonyl Compounds and Allylic Silanes
Zhao, Kai,Loh, Teck-Peng
supporting information, p. 16764 - 16772 (2016/02/12)
A highly enantioselective conjugate addition of Grignard reagents to 3-silyl unsaturated esters to deliver synthetically useful chiral β-silylcarbonyl compounds was developed. The synthetic value of this methodology was further illustrated by the synthesis of enantioenriched β-hydroxyl esters and the facile access granted to various α-chiral allylic silanes. A plethora of diastereoselective transformations of β-silylenolates were also investigated and afforded manifold organosilanes that contained contiguous stereogenic centers with excellent enantioselectivity.
Activation of Si-Si bonds for copper(I)-catalyzed conjugate silylation
Iannazzo, Laura,Molander, Gary A.
, p. 4923 - 4926,4 (2020/08/24)
Several alkyl- and vinylsilanes were prepared through the copper(I)-catalyzed conjugate silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poo
Synthesis and application of a new selenoplatinum catalyst
Arsenyan, Pavel,Oberte, Kristine,Rubina, Kira,Belyakov, Sergey
, p. 1001 - 1003 (2007/10/03)
The reaction of 4-methyl-5-ethoxycarbonyl-1,2,3-selenadiazole with (PPh3)4Pt leads to the formation of a new platinum-containing heterocyclic system. It was found that the selenoplatinum complex is a selective catalyst for the hydrosilylation of terminal alkynes to yield β-(Z)- and β-(E)-silylethylenes.
The synthesis of 2-trialkyIsilylaziridines from vinyltrialkylsilanes or the reaction of α-chloro-α-silyl carbanions with imines
Bassindale, Alan R.,Kyle, Patricia A.,Soobramanien, Marie-Claire,Taylor, Peter G.
, p. 1173 - 1180 (2007/10/03)
Three methods have been employed in the synthesis of 2-trialkylsilylaziridines. Firstly, reacting α-chloroa-silyl carbanions with imines. Secondly, from the corresponding vinylsilane, via addition of bromoazide to give the l-bromo-2-azide, followed by red
Total synthesis of (+)-aloperine. Use of a nitrogen-bound silicon tether in an intramolecular diels-alder reaction
Brosius, Arthur D.,Overman, Larry E.,Schwink, Lothar
, p. 700 - 709 (2007/10/03)
Enantioselective total syntheses of aloperine (1), N-methylaloperine (2), and N-allylaloperine (3) are reported. The central element of the synthetic strategy is an intramolecular Diels-Alder reaction in which the cycloaddends are tethered by a N-silylamine linkage. The total synthesis of 1 proceeds from commercially available 3-hydroxypiperidine hydrochloride (54) and (R)-pipecolinic acid (35) by way of nine isolated and purified intermediates. The synthesis is sufficiently efficient that gram quantities of (+)-aloperine (1) can be readily prepared. Early exploratory studies also introduced a convenient method for tethering cycloaddition partners with a sulfonamide unit to realize the intramolecular Diels-Alder cycloaddition of a vinylsulfonamide: 45 → 46.
Regio- and stereochemical aspects of the palladium-catalyzed desilylation-arylation of substituted vinylsilanes
Alvisi, Davide,Blart, Errol,Bonini, Bianca Flavia,Mazzanti, Germana,Ricci, Alfredo,Zani, Paolo
, p. 7139 - 7146 (2007/10/03)
The palladium-catalyzed desilylation-arylation of substituted vinylsilanes by p-iodoanisole in the presence of bidentate phosphine ligands is described. Apart from enhancing the rate of the reaction considerably, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the chelation-controlled desilylation-arylation reaction involving five- and six-membered chelate rings is proposed.
Allylsilanes in organic synthesis; convenient preparation of synthetic intermediates by catalytic hydrosilation of acetylenic alcohols
Murphy,Spencer,Procter
, p. 1051 - 1054 (2007/10/02)
Synthetically useful vinylsilane-alcohols such as (1) can be easily prepared by the catalytic hydrosilation of the appropriate acetylenic alcohols in high yield, and with excellent regio- and stereoselectivity, without the need to protect the hydroxyl gro
The Catalyzed Reaction of α,β-Unsaturated Esters with Various Hydrosilanes
Takeshita, Kenji,Seki, Yoshio,Kawamoto, Kazuaki,Murai, Shinji,Sonoda, Noboru
, p. 4864 - 4868 (2007/10/02)
The Co2(CO)8-catalyzed reaction of acrylic acid esters (methyl acrylate, ethyl acrylate, and butyl acrylate) with HSiEt2Me gave the corresponding (E)-3-silylacrylate in high yields, along with only a small amount of β-adducts, when the esters were used in
HYDROSILYLATION OF THE CC TRIPLE BOND BY PHENYL- AND THIENYL-SILANES
Lukevics, E.,Sturkovich, R. Ya.,Pudova, O. A.
, p. 151 - 158 (2007/10/02)
The effects of the structures of the hydrosilane and the acetylene derivative, catalyst, temperature and solvent on the yields and ratio of isomers during the hydrosilylation of phenylacetylene, 2-(ethynyl)thiophene, methyl propiolate, propargyl alcohol a
Synthesis of 3-Silylacrylates by Co2(CO)8-catalysed Reaction of Methyl Acrylate with Hydrosilanes
Takeshita, Kenji,Seki, Yoshio,Kawamoto, Kazuaki,Murai, Shinji,Sonoda, Noboru
, p. 1193 (2007/10/02)
The reaction of an excess of methyl acrylate with hydrosilanes using Co2(CO)8 as a catalyst gives methyl (E)-3-silylacrylates in high yields.
