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Volume 24
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Article

Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis

by
Yumeng Liang
1,
Mayaka Maeno
1,
Zhengyu Zhao
1 and
Norio Shibata
1,2,*
1
Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555, Japan
2
Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(15), 2774; https://doi.org/10.3390/molecules24152774
Submission received: 5 July 2019 / Revised: 25 July 2019 / Accepted: 29 July 2019 / Published: 30 July 2019
(This article belongs to the Special Issue Fabulous Fluorine in Organic and Medicinal Chemistry)
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Abstract

The organo-catalyzed enantioselective benzylation reaction of α-trifluoromethoxy indanones afforded α-benzyl-α-trifluoromethoxy indanones with a tetrasubstituted stereogenic carbon center in excellent yield with moderate enantioselectivity (up to 57% ee). Cinchona alkaloid-based chiral phase transfer catalysts were found to be effective for this transformation, and both enantiomers of α-benzyl-α-trifluoromethoxy indanones were accessed, depended on the use of cinchonidine and cinchonine-derived catalyst. The method was extended to the enantioselective allylation reaction of α-trifluoromethoxy indanones to give the allylation products in moderate yield with good enantioselectivity (up to 76% ee).
Keywords: trifluoromethoxy; fluorine; enantioselective; phase-transfer catalyst; organo-catalysis trifluoromethoxy; fluorine; enantioselective; phase-transfer catalyst; organo-catalysis
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MDPI and ACS Style

Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules 2019, 24, 2774. https://doi.org/10.3390/molecules24152774

AMA Style

Liang Y, Maeno M, Zhao Z, Shibata N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules. 2019; 24(15):2774. https://doi.org/10.3390/molecules24152774

Chicago/Turabian Style

Liang, Yumeng, Mayaka Maeno, Zhengyu Zhao, and Norio Shibata. 2019. "Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis" Molecules 24, no. 15: 2774. https://doi.org/10.3390/molecules24152774

APA Style

Liang, Y., Maeno, M., Zhao, Z., & Shibata, N. (2019). Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules, 24(15), 2774. https://doi.org/10.3390/molecules24152774

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