Communication

Chiral Phosphoric Acid Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with Nitroalkenes: Cooperative Effect of 3 Å Molecular Sieves^†

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

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Kohei Fuchibe Dr.

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

Present address: Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Japan

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Takahiko Akiyama Prof. Dr.

takahiko.akiyama@gakushuin.ac.jp

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

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Junji Itoh Dr.

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

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Kohei Fuchibe Dr.

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

Present address: Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Japan

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Takahiko Akiyama Prof. Dr.

takahiko.akiyama@gakushuin.ac.jp

Department of Chemistry, Faculty of Science, Gakushuin University, 1‐5‐1 Mejiro, Toshima‐ku, Tokyo 171‐8588, Japan, Fax: (+81) 3‐5992‐1029

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First published: 06 May 2008

https://doi.org/10.1002/anie.200800770

Citations: 225

^†

This work was partially supported by a Grant‐in Aid for Scientific Research on Priority Areas “Advanced Molecular Transformation of Carbon Resources” from the Ministry of Education, Science, Sports, Culture, and Technology (Japan). J.I. thanks the JSPS Research Fellowships for Young Scientists.

Abstract

Crafty catalysts: Friedel–Crafts alkylation of indoles with nitroalkenes proceeded in the presence of phosphoric acid 1 and 3 Å molecular sieves to give Friedel–Crafts adducts with excellent enantioselectivities (see scheme).