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Synfacts 2008(8): 0884-0884  
DOI: 10.1055/s-2008-1077927
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Friedel-Crafts Reaction of Imines with Indoles

Contributor(s): Yasuhiro Uozumi, Takao Osako
P. Yu, J. He*, C. Guo
Beijing University of Chemical Technology, P. R. of China
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

9-Thiourea epi-quinine supported on mesoporous SBA-15 material (SBA-15-SQT) was prepared by the treatment of SBA-15 with (MeO)3Si(CH2)3SH, followed by the reaction with 9-thiourea epi-quinine in the presence of AIBN. SBA-15-SQT catalyzed the asymmetric Friedel-Crafts reaction of indoles with aryl imines to give the corresponding 3-substituted indoles in 0-76.8% yield with 0-99.2% ee (6 examples). In the reaction of N-benzylidenebenzenesulfonamide with indole, the catalyst was recovered by simple filtration and reused three times without loss of enantioselectivity (1st reuse: 94.4% ee; 2nd reuse: 96.4% ee; 3rd reuse: 95.8% ee).