Catalytic stereoselective cascade reactions of quinols with trifluoromethyl ketones: direct access to CF3-containing 1,3-dioxolanes

A general and efficient synthesis of CF3-containing 1,3-dioxolanes using Et3N-catalyzed ketalization/oxa-Michael cascade of quinols with trifluoromethyl ketones is described. The reaction works efficiently under mild reaction conditions and produces the desired products in 68%-95% yields with accept...

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Veröffentlicht in:Organic & biomolecular chemistry 2016-04, Vol.14 (16), p.3981-3988
Hauptverfasser: Li, Feng, Wang, Jingjing, Xu, Mengmeng, Zhao, Xiaobo, Zhou, Xiaohong, Zhao, Wen-Xian, Liu, Lantao
Format: Artikel
Sprache:eng
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Zusammenfassung:A general and efficient synthesis of CF3-containing 1,3-dioxolanes using Et3N-catalyzed ketalization/oxa-Michael cascade of quinols with trifluoromethyl ketones is described. The reaction works efficiently under mild reaction conditions and produces the desired products in 68%-95% yields with acceptable diastereoselectivities. In addition, the reaction proceeds smoothly to give the desired product 3a in 92% yield and with high ee (80%) in the presence of a chiral catalyst (DHQ)2PHAL.
ISSN:1477-0539
DOI:10.1039/c6ob00281a