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Communication | Special issue | Vol 77, No. 2, 2009, pp.817-824
Published online, 2nd October, 2008
DOI: 10.3987/COM-08-S(F)93
Asymmetric Lewis Acid Catalysis of Aluminum (Salalen) Complexes: Friedel-Crafts Reaction of Indole

Keitaro Suyama, Kazuhiro Matsumoto, and Tsutomu Katsuki*

*Department of Chemistry, Graduate School, Faculty of Science, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

We examined the Lewis acid catalysis of chiral Al(salalen)X complexes and found that complex 1b (X = Br) serves as an efficient catalyst for the Friedel-Crafts reaction of indole with N-[(E)-alkenoyl]oxazolidin-2-ones. High enantioselectivity (up to 98% ee) was obtained under the optimized conditions.