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Synfacts 2006(4): 0357-0357  
DOI: 10.1055/s-2006-934340
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Friedel-Crafts Alkylations of Indoles with Nitroalkenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
Y. Jia, S. Zhu, Y. Yang, Z. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The authors have achieved reasonable enantiomeric excesses with the use of nitro­alkenes as the acceptors. This result nicely broadens the scope of this reaction. A very nice screening of various Lewis acids, ligands, and ­solvents was performed leading to Zn(OTf)2, Ph-bisoxazoline and toluene as the optimal reagents. Unsubstituted indoles gave high yields and good enantioselectivity with a variety of aryl-substituted nitroalkenes (many ee’s >80%).