Synfacts 2010(6): 0684-0684  
DOI: 10.1055/s-0029-1219973
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Zinc-Catalyzed Enantioselective Friedel-Crafts Alkylation

Contributor(s): Hisashi Yamamoto, Jiajing Tan
Y. Huang, E. Tokunage, S. Suzuki, M. Shiro, N. Shibata*
Nagoya Institute of Technology and Rigaku Corporation, Akishima, Japan
Further Information

Publication History

Publication Date:
20 May 2010 (online)

Significance

The first Lewis acid catalyzed enantioselective Friedel-Crafts alkylation of pyrroles and indoles with β-CF3 acrylates was presented. Excellent yields (90-99%) and high ee values (75-99%) of the resulting chiral trifluoro-methylated products were obtained. The chiral product was also used to synthesize unreported trifluorinated heliotridane.