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Organocatalyzed Enantioselective Synthesis of Quaternary Carbon‐Containing Isoindolin‐1‐ones
Author(s) -
Yu Xiaolei,
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.201100163
Subject(s) - chemistry , enantioselective synthesis , phosphoric acid , organocatalysis , quaternary carbon , catalysis , organic chemistry , recrystallization (geology) , alkylation , friedel–crafts reaction , combinatorial chemistry , paleontology , biology
3,3′‐Triphenylsilyl‐substituted ( S )‐BINOL‐based (1,1′‐bi‐2‐naphthol) phosphoric acid has proven to be an effective organocatalyst for the asymmetric Friedel–Crafts alkylation of indoles with 3‐substituted 3‐hydroxyisoindolin‐1‐ones, affording the corresponding quaternary carbon‐containing 3,3‐disubstituted isoindolin‐1‐ones in good yields (up to 99 %) with good to excellent enantioselectivities (up to 95 % ee ). The optical purity of the product was further improved after a single recrystallization. This protocol provides a convenient method for the catalytic asymmetric synthesis of valuable 3,3‐disubstituted isoindolin‐1‐ones in high yields and enantioselectivities.