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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... Full description

Journal Title: Organic letters May 19, 2017, Vol.19(10), pp.2634-2637
Main Author: Wang, Pei
Other Authors: Li, Hong-Feng , Zhao, Jia-Zhen , Du, Zhi-Hong , Da, Chao-Shan
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1523-7052 ; DOI: 10.1021/acs.orglett.7b00828
Link: http://search.proquest.com/docview/1896415003/?pq-origsite=primo
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title: Organocatalytic Enantioselective Cross-Aldol Reaction of o-Hydroxyarylketones and Trifluoromethyl Ketones.
format: Article
creator:
  • Wang, Pei
  • Li, Hong-Feng
  • Zhao, Jia-Zhen
  • Du, Zhi-Hong
  • Da, Chao-Shan
subjects:
  • Chemistry
ispartof: Organic letters, May 19, 2017, Vol.19(10), pp.2634-2637
description: 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.
language: eng
source:
identifier: E-ISSN: 1523-7052 ; DOI: 10.1021/acs.orglett.7b00828
fulltext: fulltext
issn:
  • 15237052
  • 1523-7052
url: Link


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descriptionThe 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.
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