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

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...

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Bibliographic Details
Published in:Organic letters 2017-05, Vol.19 (10), p.2634-2637
Main Authors: Wang, Pei, Li, Hong-Feng, Zhao, Jia-Zhen, Du, Zhi-Hong, Da, Chao-Shan
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00828