Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 16, Pages 3060-3066Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100163
Keywords
Synthetic methods; Asymmetric catalysis; Enantioselectivity; Nitrogen heterocycles; Alkylation
Categories
Funding
- National Natural Science Foundation of China [20772058, 20972070]
- National Basic Research Program of China (973 program) [2010CB833300]
- Key Laboratory of Elemento-Organic Chemistry
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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.
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