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Synthesis 2012; 44(23): 3590-3594
DOI: 10.1055/s-0032-1317161
DOI: 10.1055/s-0032-1317161
practical synthetic procedures
Enantioselective Synthesis of Substituted Indoles Through Zirconium(IV)-Catalyzed Friedel–Crafts Alkylation
Further Information
Publication History
Received: 01 June 2012
Accepted after revision: 02 August 2012
Publication Date:
23 August 2012 (online)
Abstract
The chiral complex of (R)-3,3′-Br2-BINOL and zirconium tert-butoxide catalyzes the Friedel–Crafts alkylation of indoles with enones bearing an alkyl or fluorinated group at the β-position to give indoles having a side chain at the C3 position with a tertiary stereogenic center in good yields and with excellent enantioselectivities.
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For reviews on enantioselective Friedel–Crafts reactions, see:
For some recent examples involving 1,2-addition of indoles, see also:
For some recent examples with aromatic compounds other than indoles, see also:
For some examples, see: With enones:
With nitroalkenes:
For some examples, see: