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Efficient Catalytic Kinetic Resolution of Spiro‐epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles
Author(s) -
Zhu Gongming,
Bao Guangjun,
Li Yiping,
Sun Wangsheng,
Li Jing,
Hong Liang,
Wang Rui
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700494
Subject(s) - kinetic resolution , alkylation , oxindole , catalysis , enantioselective synthesis , friedel–crafts reaction , indole test , methanol , chemistry , phosphoric acid , enantiomer , organic chemistry , combinatorial chemistry
An efficient process involving the catalytic kinetic resolution of racemic spiro‐epoxyoxindoles with the simultaneous enantioselective Friedel–Crafts alkylation of indoles has been realized using a chiral phosphoric acid catalyst. The reaction provides two useful intermediates in high yields and excellent enantioselectivities. Performing the catalysis on a gram scale led to (R)‐3‐(3‐indolyl)‐oxindole‐3‐methanol, which was used in the asymmetric formal total synthesis of (+)‐gliocladin C. Notably, the enantiomers (S)‐3‐(3‐indolyl)‐oxindole‐3‐methanol can be obtained easily by the reaction of the resolved spiro‐epoxyoxindole with indole.