89359-17-1Relevant articles and documents
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
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
, 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.
Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst
Xu, Hua-Jian,Zhu, Feng-Fei,Shen, Yong-Ya,Wan, Xin,Feng, Yi-Si
, p. 4145 - 4151 (2012/07/27)
Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
, p. 17023 - 17026,4 (2012/12/12)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
, p. 17023 - 17026 (2013/01/15)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Efficient asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones using new polymer-supported and unsupported chiral co(salen) complexes
Sandaroos, Reza,Goldani, Mohammad Taghi,Damavandi, Saman,Mohammadi, Ali
, p. 871 - 876,6 (2020/09/09)
Two heterogeneous catalysts 4 and 5 and three homogenous complexes 1-3 were prepared and used for enantioselective Baeyer-Villiger (B-V) oxidation of prochiral cyclobutanones. Among the prepared catalysts, the supported ones showed better enantioselectivi
