112606-95-8Relevant academic research and scientific papers
Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere
Tang, Yitian,Shen, Chaoren,Yao, Qiyi,Tian, Xinxin,Wang, Bo,Dong, Kaiwu
, p. 5898 - 5902 (2020/10/02)
A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.
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.).
Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium
Sakai, Norio,Horikawa, Shuhei,Ogiwara, Yohei
, p. 565 - 574 (2017/12/26)
The direct conversion of lactones into thiolactones with elemental sulfur (S 8) catalyzed by InCl 3 /PhSiH 3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.
Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions
Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.
supporting information, p. 36 - 39 (2018/01/17)
A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.
Gallium-catalyzed reductive lactonization of γ-keto acids with a hydrosilane
Sakai, Norio,Horikawa, Shuhei,Ogiwara, Yohei
, p. 81763 - 81766 (2016/09/09)
Described herein is the GaCl3-catalyzed lactonization of γ-keto carboxylic acids in the presence of PhSiH3 leading to the direct preparation of γ-lactone derivatives. This reducing system showed a relatively wide functional group tolerance.
MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 2628 - 2631 (2016/02/18)
An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
, p. 4958 - 4961,4 (2012/12/12)
A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
, p. 4958 - 4961 (2013/01/15)
A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent suzuki cross-couplings
Zultanski, Susan L.,Fu, Gregory C.
supporting information; experimental part, p. 15362 - 15364 (2011/11/11)
With the aid of a chiral nickel catalyst, enantioselective γ- (and I-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.
Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts
Cossy, Janine,Bargiggia, Frederic,BouzBouz, Samir
, p. 459 - 462 (2007/10/03)
(Matrix presented) A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.
