Organic Letters
Organic Letters
5 years ago

Organocatalytic Enantioselective Cross-Aldol Reaction of o-Hydroxyarylketones and Trifluoromethyl Ketones

Organocatalytic Enantioselective Cross-Aldol Reaction of o-Hydroxyarylketones and Trifluoromethyl Ketones
Jia-Zhen Zhao, Zhi-Hong Du, Chao-Shan Da, Hong-Feng Li, Pei Wang
The enantioselective cross-aldol reaction between o-hydroxyacetophenones and trifluoromethyl ketones catalyzed by chiral thiourea organocatalysts is reported. Gram-scale synthesis of the cross-aldol product was carried out, with no decrease in the yield and enantioselectivity. Furthermore, the cross-aldol products thus prepared were used in the preparation of medicinally interesting 3,5-diaryl-5-trifluoromethyl-2-isoxazoline and β-trifluoromethyl-β-tertiary hydroxy acid ester with high yield and enantiopurity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00828

DOI: 10.1021/acs.orglett.7b00828

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