89359-16-0Relevant articles and documents
Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates
Ji, Xiaolei,Shen, Chaoren,Tian, Xinxin,Dong, Kaiwu
, p. 8645 - 8649 (2021/10/25)
A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.
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.
Synthesis method of butyrolactone compound
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Paragraph 0019-0054, (2020/07/21)
The invention relates to a synthesis method of a butyrolactone compound. The synthesis method comprises the following step: in the presence of a solvent and a cobalt catalyst, converting an oxetane compound shown as general formula I into a butyrolactone compound shown as general formula II through carbonyl insertion ring expansion reaction in an atmosphere of CO and H2. Compared with an existingmethod for synthesizing butyrolactone through oxetane carbonylation ring expansion reaction in a carbon monoxide atmosphere, the synthesis method of a butyrolactone compound provided by the inventionhas the advantages of excellent catalytic activity, excellent chemical selection, wide substrate applicability, mild reaction conditions and the like; compared with other methods for synthesizing butyrolactone compounds, the method provided by the invention has the advantages of wide substrate range, high atom economy, no need of noble metal catalysis and the like, therefore the method has a wideapplication prospect.
Enantioselective Rh-Catalyzed Anti-Markovnikov Hydroformylation of 1,1-Disubstituted Allylic Alcohols and Amines: An Efficient Route to Chiral Lactones and Lactams
You, Cai,Li, Shuailong,Li, Xiuxiu,Lv, Hui,Zhang, Xumu
, p. 8529 - 8533 (2019/09/12)
Rh-catalyzed highly enantioselective anti-Markovnikov hydroformylation of 1,1-disubstituted allylic alcohols and amines has been achieved. By using a chiral hybrid phosphorus ligand, a series of challenging 1,1-disubstituted allylic alcohols and amines we
Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents
Khatun, Nilufa,Kim, Myeong Jun,Woo, Sang Kook
supporting information, p. 6239 - 6243 (2018/09/27)
A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids,-butyrolactones, and complex aryl alkyl ethers.
Determination of the absolute configuration of two αvβ6 integrin inhibitors for the treatment of idiopathic pulmonary fibrosis and investigations on the asymmetric 1,4-addition of arylboronic acids to crotonate esters bearing a C4-oxygen substituent
Procopiou, Panayiotis A.,Barrett, Tim N.,Copley, Royston C.B.,Tame, Christopher J.
, p. 1384 - 1393 (2017/11/09)
The absolute configuration of two novel αvβ6 integrin inhibitors was established via degradation to the corresponding C3-aryl substituted butyrolactone. The configuration of the resulting lactones was established by asymmetric synthesis using 1,4-addition of arylboronic acids to butenolide, catalysed by bis(norbornadiene)rhodium (I) tetrafluoroborate in the presence of (R)-BINAP, and confirmed by X-ray crystallography. Studies on arylboronic acid conjugate additions to acyclic crotonate esters bearing a γ-oxygen substituent are also reported. Three Rh catalysts were investigated and the one giving the highest enantioselectivity was bis(norbornadiene)rhodium (I) tetrafluoroborate.
Manipulating the stereoselectivity of the thermostable Baeyer-Villiger monooxygenase TmCHMO by directed evolution
Li, Guangyue,Fürst, Maximilian J. L. J.,Mansouri, Hamid Reza,Ressmann, Anna K.,Ilie, Adriana,Rudroff, Florian,Mihovilovic, Marko D.,Fraaije, Marco W.,Reetz, Manfred T.
, p. 9824 - 9829 (2017/12/08)
Baeyer-Villiger monooxygenases (BVMOs) and evolved mutants have been shown to be excellent biocatalysts in many stereoselective Baeyer-Villiger transformations, but industrial applications are rare which is partly due to the insufficient thermostability o
Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones
Rodríguez-Mata, María,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente,García-Cerrada, Susana,Mendiola, Javier,de Frutos, óscar,Collado, Iván
supporting information, p. 7268 - 7275 (2016/10/26)
A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.
Lactonization reactions through hydrolase-catalyzed peracid formation. Use of lipases for chemoenzymatic Baeyer-Villiger oxidations of cyclobutanones
González-Martínez, Daniel,Rodríguez-Mata, María,Méndez-Sánchez, Daniel,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 31 - 36 (2015/04/14)
A one-pot chemoenzymatic method has been described for the synthesis of γ-butyrolactones starting from the corresponding ketones through a Baeyer-Villiger reaction. The approach is based on a lipase-catalyzed perhydrolysis for the formation of peracetic acid, which is the responsible for the ketone oxidation. Optimization studies have been performed in the oxidation of cyclobutanone, finding Candida antarctica lipase type B, ethyl acetate and urea-hydrogen peroxide complex as the best system. The relative ratio of these reagents has also been analyzed in depth. This synthetic approach has been successfully extended to a family of 3-substituted cyclobutanones in high substrate concentration, yielding the corresponding lactones with excellent isolated yields and purities, under mild reaction conditions and after a simple extraction protocol.
Stable chiral complexes of ionic liquids with Aluminium and biaryl ligands as efficient catalysts for the synthesis of chiral lactones
Drozdz, Agnieszka,Foreiter, Magdalena B.,Chrobok, Anna
, p. 559 - 563 (2014/03/21)
A new catalytic system for the asymmetric Baeyer-?Villiger oxidation of monosubstituted prochiral cyclobutanones to γ-butyrolactones with high yields (40-99%) and enantioselectivities (45-87%) is described. Aluminium complexes with biaryl ligands and ioni
