Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Efficient Catalytic Kinetic Resolution of Spiro-epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles

Efficient Catalytic Kinetic Resolution of Spiro-epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles
Liang Hong, Guangjun Bao, Yiping Li, Jing Li, Rui Wang, Wangsheng Sun, Gongming Zhu
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. Crafty: 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. One of the intermediates was used in the asymmetric formal total synthesis of (+)-gliocladin C.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700494

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