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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)