77620-05-4Relevant articles and documents
Indium-Catalyzed C?F Bond Transformation through Oxymetalation/β-Fluorine Elimination to Access Fluorinated Isocoumarins
Yata, Tetsuji,Nishimoto, Yoshihiro,Chiba, Kouji,Yasuda, Makoto
, p. 8288 - 8294 (2021/05/21)
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.
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
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
, p. 6366 - 6369 (2015/01/16)
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.
An indium-mediated allylative/transesterification DFT-directed approach to chiral C(3)-functionalized phthalides
Mirabdolbaghi, Roya,Dudding, Travis
, p. 3748 - 3751 (2012/09/07)
A one-pot synthesis of chiral C(3)-substituted phthalides via an indium-mediated allylation/transesterification reaction is described. The development of this reaction was facilitated through the applied use of DFT calculations to rationalize the stereoselection of a chiral In-mediated process. It was discovered that the enantiomeric excess of this reaction depended upon the steric size, chain length, and substitution of the aldehyde employed.
