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1. Asymmetric synthesis of chiral trifluoromethylated heliotridane viahighly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrrolesWe briefly communicated this work in 2010.23In the present paper, we describe in full the results of our highly catalytic asymmetric Friedel–Crafts alkylation.Electronic supplementary information (ESI) available: General experimental procedures, 1H, 13C and 19F NMR spectra for all crossed products, characterisation data for all new products. CCDC 758056. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1nj20550a

Author

Huang, Yiyong, Suzuki, Satoru, Liu, Guokai, Tokunaga, Etsuko, Shiro, Motoo, and Shibata, Norio

Subjects
*ASYMMETRY (Chemistry), *CHIRALITY, *PYRROLIZIDINES, *ORGANIC synthesis, *CATALYSTS, *ACRYLATES, *PYRROLES, *CHEMICAL reactions
Abstract

Chiral Ph-dbfox (Ph-dbfox = (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline))/Zn(NTf2)2catalyzed enantioselective Friedel–Crafts reactions of β-CF3acrylates with pyrroles and indoles have been investigated, which afforded the corresponding chiral trifluoromethyl pyrrole and indole derivatives in high yields (90–99%) with a range of 66–99% ee values. With the aid of the chiral adduct of the asymmetric Friedel–Crafts reaction, the chiral trifluoromethylated heliotridane has been successfully constructed in good total yield. [ABSTRACT FROM AUTHOR]

Published
2011
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