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Chiral Phosphoric Acid Catalyzed Asymmetric Friedel–Crafts Alkylation of Indole with 3‐Hydroxyisoindolin‐1‐one: Enantioselective Synthesis of 3‐Indolyl‐Substituted Isoindolin‐1‐ones
Author(s) -
Yu Xiaolei,
Lu Aidang,
Wang Youming,
Wu Guiping,
Song Haibin,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2011
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.201001408
Subject(s) - chemistry , friedel–crafts reaction , phosphoric acid , alkylation , catalysis , indole test , organic chemistry , recrystallization (geology) , enantioselective synthesis , organocatalysis , combinatorial chemistry , paleontology , biology
Chiral phosphoric acids have been proven to be effective organocatalysts for the asymmetric Friedel–Crafts alkylation of indoles with 3‐hydroxyisoindolin‐1‐ones. The corresponding products were obtained in excellent chemical yields (up to 99 %) with moderate to excellent enantioselectivities (up to >99 % ee after a single recrystallization). This is the first example of the catalytic asymmetric synthesis of valuable 3‐substituted isoindolin‐1‐ones in high yields and enantioselectivities.