Remarkable effect of N-substituent on enantioselective ruthenium-catalyzed propargylation of indoles with propargylic alcohols.
Ruthenium-catalyzed enantioselective propargylation of indoles with propargylic alcohols affords the corresponding beta-propargylated indoles in good yields with a high enantioselectivity (up to 95% ee). A remarkable effect of the nature of the N-substituent of indoles is observed for the enantioselectivity of the propargylated indoles. The preparative method described in this paper may provide a novel protocol for asymmetric Friedel-Crafts alkylation of indoles using propargylic alcohols as a new type of electrophiles.
Matsuzawa
Hiroshi
H
Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113-8656, Japan.
Kanao
Keiichiro
K
Miyake
Yoshihiro
Y
Nishibayashi
Yoshiaki
Y
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D007211:Indoles; D020005:Propanols; D012428:Ruthenium; C028255:propargyl alcohol