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Open AccessArticle

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

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
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)
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). View Full-Text
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.

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