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Synlett 2009(10): 1639-1642  
DOI: 10.1055/s-0029-1217324
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© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Enantioselective Aza-Friedel-Crafts Alkylation of Pyrroles with N-(Heteroarenesulfonyl)imines

Shuichi Nakamura*, Yuki Sakurai, Hiroki Nakashima, Norio Shibata, Takeshi Toru
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
Fax: +81(52)7355442; e-Mail: snakamur@nitech.ac.jp;
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Publication History

Received 2 February 2009
Publication Date:
02 June 2009 (online)

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Abstract

Organocatalytic enantioselective aza-Friedel-Crafts alkylation of pyrroles with imines having heteroarylsulfonyl groups catalyzed by binaphthol monophosphoric acids afforded products with high enantioselectivity (up to 95% ee).

Key words

amines - Asymmetric synthesis - aza-Friedel-Crafts alkylation - heteroarylsulfonyl group - organocatalysis

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12

We also examined several chiral Lewis acids, such as Box-Mg(II), Box-Cu(II), and BINAP-Pd(II), giving the product 2a in low yield.

13

We also examined the reaction in cumene, benzene, CH2Cl2, Et2O, EtOH, and MeCN, using 3b giving the product 2a with lower enantioselectivity than that in toluene.

14

Unfortunately, aliphatic N-(2-pyridylsulfonyl)imines could not be obtained from aliphatic aldehydes under various reaction conditions.