Synthesis of 3-Indolylglycine Derivatives via Dinuclear Zinc Catalytic Asymmetric Friedel-Crafts Alkylation Reaction.
A direct asymmetric Friedel-Crafts (F-C) alkylation reaction between a wide range of indoles and ethyl 2-(4-methoxyphenylimino)acetate catalyzed by Trost's dinuclear complex is reported. A series of 3-indolylglycine derivatives were synthesized in enantioselectivity of up to >99% enantiomeric excess (ee) using 10 mol% catalyst loading under mild conditions. This atom economic reaction could be run on a gram scale without impacting its enantioselectivity. The absolute stereochemistry of catalytic products was determined by correlation with a known configuration compound. A possible mechanism was proposed for the asymmetric induction.
College of Chemistry and Molecular Engineering, Zhengzhou University , No. 75, Daxue Street, Zhengzhou City, Henan Province 450052, P. R. China.
Xin-Wei
XW
Wang
College of Chemistry and Molecular Engineering, Zhengzhou University , No. 75, Daxue Street, Zhengzhou City, Henan Province 450052, P. R. China.
Yuan-Zhao
YZ
Hua
College of Chemistry and Molecular Engineering, Zhengzhou University , No. 75, Daxue Street, Zhengzhou City, Henan Province 450052, P. R. China.
Min-Can
MC
Wang