Preprint Article Version 1 This version is not peer-reviewed

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

Version 1 : Received: 5 July 2019 / Approved: 8 July 2019 / Online: 8 July 2019 (12:23:52 CEST)

How to cite: Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Preprints 2019, 2019070093 (doi: 10.20944/preprints201907.0093.v1). Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Preprints 2019, 2019070093 (doi: 10.20944/preprints201907.0093.v1).

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).

Subject Areas

trifluoromethoxy; fluorine; enantioselective; phase-transfer catalyst; organo-catalysis

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