Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules2019, 24, 2774.
Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules 2019, 24, 2774.
Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules2019, 24, 2774.
Liang, Y.; Maeno, M.; Zhao, Z.; Shibata, N. Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis. Molecules 2019, 24, 2774.
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).
Chemistry and Materials Science, Organic Chemistry
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