103024-10-8Relevant articles and documents
Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones
Okamoto, Kazuhiro,Shimbayashi, Takuya,Tamura, Eisuke,Ohe, Kouichi
, p. 5843 - 5845 (2015)
We have developed an indium-catalyzed [2 + 2] cycloaddition of allylsilanes to alkynones leading to selective cyclobutenone formation. The resulting cyclobutenones were readily converted to the oxidized products by Tamao-Fleming oxidation or the ring-open
Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon
Horino, Yoshikazu,Ishibashi, Mayo,Nakasai, Kosuke,Korenaga, Toshinobu
supporting information, (2020/08/28)
The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.
Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction
Shintani, Ryo,Okamoto, Kazuhiro,Hayashi, Tamio
, p. 4757 - 4759 (2007/10/03)
(Chemical Equation Presented) A new synthetic method for chiral organosilicon compounds through a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-silyl α,β-unsaturated carbonyl compounds has been developed. By employing (R,R)-Bn-bod * as a ligand, a range of arylboronic acids can be coupled with these substrates in very high enantiomeric excess. The resulting β-silyl 1,4-adducts can be converted to β-hydroxy carbonyl compounds or allylsilanes while retaining their stereochemical information.
ALDEHYDE-SELECTIVE ADDITION OF ALKYNYLCHROMIUM COMPOUNDS PREPARED BY REDUCTION OF ALKYNYL HALIDES WITH CHROMIUM(II) REAGENT
Takai, Kazuhiko,Kuroda, Tooru,Nakatsukasa, Shigeki,Oshima, Koichiro,Nozaki, Hitosi
, p. 5585 - 5588 (2007/10/02)
Alkynyl halides are reduced by chromium(II) chloride in DMF to give unisolable alkynylchromium compounds which add selectivity to an aldehyde moiety without affecting the coexisting ketone group of the substrate.
