Chiral Brønsted‐Acid‐Catalyzed Enantioselective Arylation of Ethyl Trifluoroacetoacetate and Ethyl Trifluoropyruvate | Zendy

Nie Jing | Zendy; Zhang GuangWu | Zendy; Wang Lian | Zendy; Zheng DongHua | Zendy; Zheng Yan | Zendy; Ma JunAn | Zendy

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Chiral Brønsted‐Acid‐Catalyzed Enantioselective Arylation of Ethyl Trifluoroacetoacetate and Ethyl Trifluoropyruvate

Author(s) -

Nie Jing,

Zhang GuangWu,

Wang Lian,

Zheng DongHua,

Zheng Yan,

Ma JunAn

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900353

Subject(s) - chemistry , enantioselective synthesis , phosphoric acid , catalysis , recrystallization (geology) , organic chemistry , trifluoromethyl , cinchona alkaloids , brønsted–lowry acid–base theory , lewis acids and bases , cinchona , alkyl , paleontology , biology

Chiral phosphoric acid was found to be an effective organocatalysts for the direct enantioselective arylation of ethyl 4,4,4‐trifluoroacetoacetate (ETFAA). A series of chiral trifluoromethyl‐substituted tertiary alcohols were obtained in moderate to high yields with up to 78 % ee . Several desired products were obtained with excellent optical purities after a single recrystallization. This method was also extended to ethyl trifluoropyruvate, which is complementary to systems catalyzed by Lewis acids and cinchona alkaloids.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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