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. 2006 Jun 28;128(25):8156-7.
doi: 10.1021/ja062700v.

Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst

Yong-Qiang Wang  1 , Jun Song, Ran Hong, Hongming Li, Li Deng
Affiliations

Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst

Yong-Qiang Wang et al. J Am Chem Soc. .

Abstract

In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines. This establishes a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives.

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Figures

Scheme 1
Scheme 1
A General Approach toward 3-Indolyl Methanamines 3 via Enantioselective Friedel-Crafts Reaction
Scheme 2
Scheme 2
Conversion of N-Ts to N-CBz 3-indoly-methanamine 8
See this image and copyright information in PMC

References

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    1. For recent reviews of catalytic asymmetric Friedel-Crafts reactions see: Bandini M, Melloni A, Umani-Ronchi A. Angew. Chem., Int. Ed. 2004;43:550. Jørgensen KA. Synthesis. 2003:1117.

    1. For select examples of catalytic asymmetric Michael additions of indoles by chiral metal complexes see: Evans DA, Scheidt KA, Fandrick KR, Lam HW, Wu J. J. Am. Chem. Soc. 2003;125:10780. Evans DA, Fandrick KR, Song H-J. J. Am. Chem. Soc. 2005;127:8942. Palomo C, Oiarbide M, Kardak BG, Garcia JM, Linden A. J. Am. Chem. Soc. 2005;127:4154.

    1. For Michael additions of indoles catalyzed by chiral organic catalysts see: Austin JF, MacMillan DWC. J. Am. Chem. Soc. 2002;124:1172. Huang Y, Walji AM, Larsen CH, MacMillan DWC. J. Am. Chem. Soc. 2005;127:15051. Austin JF, Kim S-G, Sinz CJ, Xiao W-J, MacMillan DWC. Proc. Natl. Acad. Sci USA. 2004;101:5482. Herrera RP, Sgarzani V, Bernardi L, Ricci A. Angew. Chem. Int. Ed. 2005;44:6576.

    1. For catalytic asymmetric additions of indoles to ethyl 3,3,3-trifluoropyruvate see: Zhuang W, Gathergood N, Hazell RG, Jørgensen KA. J. Org. Chem. 2001;66:1009. Török B, Abid M, London G, Esquibel J, Török MS, Mhadgut C, Yan P, Prakash GKS. Angew. Chem. Int. Ed. 2005;44:3086.

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