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Hirano K, Saito T, Fujihira Y, et al. Diastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23. J Org Chem. 2020;85(12):7976-7985doi: 10.1021/acs.joc.0c00796.
Hirano, K., Saito, T., Fujihira, Y., Sedgwick, D. M., Fustero, S., & Shibata, N. (2020). Diastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23. The Journal of organic chemistry, 85(12), 7976-7985. https://doi.org/10.1021/acs.joc.0c00796
Hirano, Kazuki, et al. "Diastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23." The Journal of organic chemistry vol. 85,12 (2020): 7976-7985. doi: https://doi.org/10.1021/acs.joc.0c00796
Hirano K, Saito T, Fujihira Y, Sedgwick DM, Fustero S, Shibata N. Diastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23. J Org Chem. 2020 Jun 19;85(12):7976-7985. doi: 10.1021/acs.joc.0c00796. Epub 2020 Jun 02. PMID: 32421330.
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J Org Chem. 2020 Jun 19;85(12):7976-7985. doi: 10.1021/acs.joc.0c00796. Epub 2020 Jun 02.

Diastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23.

The Journal of organic chemistry

Kazuki Hirano, Takuya Saito, Yamato Fujihira, Daniel M Sedgwick, Santos Fustero, Norio Shibata

Affiliations

  1. Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan.
  2. Departmento de Química Orgánica, Universitat de València, Burjassot 46100, Spain.
  3. Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China.

PMID: 32421330 DOI: 10.1021/acs.joc.0c00796

Abstract

Fluoroform, HFC-23, is an industrial byproduct from the synthesis of polytetrafluoroethylene and is a vastly underused resource; however, its physicochemical properties have hindered progress toward synthetic uses. Herein, we describe the use of HFC-23 as a cheap trifluoromethylating agent in two reactions for the highly diastereoselective synthesis of medicinally attractive chiral amines with two stereogenic carbon centers: a base-dependent, stereodivergent nucleophilic addition to synthesize enantioenriched vicinal diamines and a tandem nucleophilic addition/aza-Michael sequence toward enantioenriched isoindolines.

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