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Synthesis 2009(23): 3994-4000  
DOI: 10.1055/s-0029-1217038
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Friedel-Crafts Alkylation of Indoles with Aromatic α,β-Unsaturated Aldehydes Catalyzed by Diphenylprolinol Silyl Ether

Zhi-Jing Wanga, Jian-Guo Yangb, Jun Jina, Xin Lva, Weiliang Bao*a
a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China
Fax: +86(571)88273814; e-Mail: wlbao@css.zju.edu.cn;
b Office of Assets Administration, Taizhou University, Linhai 317000, P. R. of China
Further Information

Publication History

Received 15 June 2009
Publication Date:
12 October 2009 (online)

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Abstract

A catalytic enantioselective Friedel-Crafts alkylation of indoles with aromatic α,β-unsaturated aldehydes has been developed. The process is promoted by (S)-diphenylprolinol trimethyl silyl ether to afford, after sodium borohydride mediated reduction, 3-indolyl-3-phenylpropanols in high enantioselectivities and good yields.

Key words

organocatalysis - enantioselectivity - Friedel-Crafts alkylation - indoles - aromatic α,β-unsaturated aldehydes

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