Literature DB >> 20954725

Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane.

Hiroyuki Kawai1, Kentaro Tachi, Etsuko Tokunaga, Motoo Shiro, Norio Shibata.   

Abstract

The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me(4)NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.

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Year:  2010        PMID： 20954725     DOI： 10.1021/ol102189c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system.

Authors:  Satoshi Okusu; Yutaka Sugita; Etsuko Tokunaga; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2013-10-23       Impact factor: 2.883

Review 2.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

3.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

Authors:  Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

4.  Cs₂CO₃-Initiated Trifluoro-Methylation of Chalcones and Ketones for Practical Synthesis of Trifluoromethylated Tertiary Silyl Ethers.

Authors:  Cheng Dong; Xing-Feng Bai; Ji-Yuan Lv; Yu-Ming Cui; Jian Cao; Zhan-Jiang Zheng; Li-Wen Xu
Journal:  Molecules       Date:  2017-05-18       Impact factor: 4.411

5.  Cation versus Radical: Studies on the C/O Regioselectivity in Electrophilic Tri-, Di- and Monofluoromethylations of β-Ketoesters.

Authors:  Yu-Dong Yang; Xu Lu; Guokai Liu; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  ChemistryOpen       Date:  2012-10-11       Impact factor: 2.911
  5 in total

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