- Indium-Catalyzed C?F Bond Transformation through Oxymetalation/β-Fluorine Elimination to Access Fluorinated Isocoumarins
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Fluorinated heterocycles have attracted much attention in the pharmaceutical and agrochemical industries. Many strategies have already been developed to achieve the synthesis of fluorinated heterocycles. Formidable challenges remain, however, in the synthesis of fluorinated isocoumarin derivatives that are among the most alluring structural motifs. Herein, the indium-catalyzed C?F bond transformation of 2-(2,2-difluorovinyl) benzoates is reported, which are readily accessible compounds, to give a diverse array of fluorinated isocoumarins. The present reaction proceeds smoothly using inexpensive reagents: a catalytic amount of indium salt in the presence of zinc salt. A theoretical calculation of potential energy profiles showed that the reaction consists of oxymetalation with the elimination of alkyl halide and the β-fluorine elimination.
- Yata, Tetsuji,Nishimoto, Yoshihiro,Chiba, Kouji,Yasuda, Makoto
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supporting information
p. 8288 - 8294
(2021/05/21)
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- Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade
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A Zn-mediated propargylation/lactamization cascade reaction with chiral 2-formylbenzoate derived N-tert-butanesulfinyl imines was realized, which provided a practical and efficient method for the synthesis of chiral isoindolinones. High diastereoselectivities (up to 97:3 dr) and good reaction yields were observed for most examined cases.
- Meng, Jiao-Long,Jiao, Tang-Qian,Chen, Ya-Heng,Fu, Rui,Zhang, Shu-Sheng,Zhao, Qian,Feng, Chen-Guo,Lin, Guo-Qiang
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supporting information
p. 1564 - 1567
(2018/03/23)
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- Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization
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Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.
- He, Yuwei,Cheng, Chuyu,Chen, Bin,Duan, Kun,Zhuang, Yue,Yuan, Bo,Zhang, Meisan,Zhou, Yougui,Zhou, Zihong,Su, Yu-Jun,Cao, Rihui,Qiu, Liqin
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supporting information
p. 6366 - 6369
(2015/01/16)
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- Asymmetric organocatalytic synthesis of trans -3,4-disubstituted isochromanones via an intramolecular aldol reaction
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The diastereo- and enantioselective synthesis of 3-acetyl-4- hydroxyisochroman-1-ones via an intramolecular trans-selective aldol reaction employing proline-type organocatalysts is described. Good yields (64-88%) and high stereoselectivities (87 to >95% de, 84-99% ee) are obtained, thus potentially enabling, for example, a new direct entry to carbazolelactone alkaloid natural products. Georg Thieme Verlag Stuttgart, New York.
- Fronert, Jeanne,Bisschops, Tom,Cassens-Sasse, Elisa,Atodiresei, Iuliana,Enders, Dieter
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p. 1708 - 1712
(2013/07/19)
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- CARBAMATE COMPOUNDS AND OF MAKING AND USING SAME
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Provided herein are carbamate compounds which may be useful in the treatment of, for example, pain, solid tumors and/or obesity.
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Paragraph 00473
(2013/10/08)
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- Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes
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A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1- ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.
- Abaev, Vladimir T.,Dmitriev, Artem S.,Gutnov, Andrey V.,Podelyakin, Sergey A.,Butin, Alexander V.
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p. 1195 - 1204
(2007/10/03)
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- CASPASE INHIBITORS AND USES THEREOF
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The present invention relates to compounds of formula (I); useful as inhibitors of caspases. The present invention also provides pharmaceutically acceptable compositions comprising said compounds, processes for preparing the compounds, and methods of using the compounds and compositions in the treatment of various diseases, conditions, or disorders.
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