Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrroles
2011
Chiral Ph-dbfox (Ph-dbfox = (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline))/Zn(NTf2)2 catalyzed enantioselective Friedel–Crafts reactions of β-CF3 acrylates 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.
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