Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane.
The first chiral Lewis acid catalyzed enantioselective Friedel-Crafts alkylation of pyrroles with beta-CF(3) acrylates has been investigated, which afforded various types of chiral trifluoromethylated compounds in excellent yields (90-99%) with high ee's (up to 99% ee). With the aid of the Friedel-Crafts reaction adduct, optically active trifluorinated heliotridane was successfully constructed.
Huang
Yiyong
Y
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Tokunaga
Etsuko
E
Suzuki
Satoru
S
Shiro
Motoo
M
Shibata
Norio
N
D000179:Acrylates / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000179:Acrylates; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C518047:heliotridane