681179-34-0Relevant academic research and scientific papers
Sunlight-induced C–C bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins
Hayakawa, Mamiko,Shirota, Hisashi,Hirayama, Souta,Yamada, Ryuusei,Aoyama, Tadashi,Ouchi, Akihiko
, (2021/04/09)
A sunlight-induced C–C bond formation reactions upon the addition of alcohols/ethers/acetals to olefins proceeded efficiently using di-tert-butyl peroxide (DTBP). The reactions proceeded faster than many of the previously reported sunlight and many conventional lamp photolyses, typically in 3–4 h under irradiation with sunlight, in excellent yield using olefins bearing two electron withdrawing groups (EWGs) (product yield > 95 %) and in good to fair yield with olefins bearing one EWG. The yields observed for some products were ～20 % higher than those obtained using a conventional Xe lamp as the light source, which was confirmed to be due to a light intensity effect. Gram-scale experiments showed similar yields to those observed in their corresponding small-scale experiments.
Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C?H Alkylation of Alcohols
Sakai, Kentaro,Oisaki, Kounosuke,Kanai, Motomu
supporting information, p. 337 - 343 (2019/12/24)
The development of catalyst-controlled site-selective C(sp3)?H functionalization is a current major challenge in organic synthesis. This paper describes DFT-guided identification of pentavalent silicate species as a novel bond-weakening catalyst for the α-C?H bonds of alcohols together with a photoredox catalyst and a hydrogen atom transfer catalyst. Specifically, Martin's spirosilane accelerated α-C?H alkylation of alcohols. (Figure presented.).
Photochemical C-C bond formation between alcohols and olefins by an environmentally benign radical reaction
Ouchi, Akihiko,Liu, Chuanxiang,Kaneda, Masayuki,Hyugano, Takeshi
, p. 3807 - 3816 (2013/07/25)
A radical C-C bond formation between olefins and alcohols proceeded efficiently by simple light irradiation at room temperature. The reaction proceeded in the presence of commercially available tBuOOtBu without using the harmful elements and/or compounds that have an unpleasant smell that are often used in conventional radical reactions. In addition, the reaction did not require photosensitizers or photocatalysts, which eliminated the time-consuming separation of sensitizers after the reaction, or the synthesis of photocatalysts as reported in previous procedures. A radical C-C bond formation between olefins and alcohols proceeded efficiently by simple light irradiation at room temperature without using the harmful elements often used in conventional radical reactions. Copyright
Ru-BINAP-catalyzed asymmetric hydrogenation of keto esters in high pressure carbon dioxide
Turova, Olga V.,Kuchurov, Ilya V.,Starodubtseva, Eugenia V.,Ferapontov, Vladimir A.,Ikonnikov, Nikolai S.,Zlotin, Sergei G.,Vinogradov, Maxim G.
experimental part, p. 184 - 186 (2012/10/08)
Asymmetric hydrogenation of ethyl 4-chloro-3-oxobutyrate and dimethyl acetylsuccinate in high pressure CO2 using [RuCl2(C 6H6)]2-(R)-BINAP as the catalyst provides high ee values for the products.
A concise synthesis of highly enantiomerically enriched 2-alkylparaconic acid esters via ruthenium-catalyzed asymmetric hydrogenation of acylsuccinates
Turova, Olga V.,Starodubtseva, Eugenia V.,Vinogradov, Maxim G.,Ferapontov, Vladimir A.,Struchkova, Marina I.
experimental part, p. 2121 - 2124 (2010/03/04)
The catalytic asymmetric hydrogenation of acylsuccinates using RuCl3 as a precatalyst and atropisomeric diphosphines as chiral auxiliaries allows the synthesis of optically active 2-alkylparaconic acid esters in preparative yields with enantios
Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3- furancarboxylic acid derivatives
Comini, Andrea,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio
, p. 617 - 625 (2007/10/03)
(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using α-chymotrypsin (α-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate.
