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- Title
Efficient Catalytic Kinetic Resolution of Spiro-epoxyoxindoles with Concomitant Asymmetric Friedel-Crafts Alkylation of Indoles.
- Authors
Zhu, Gongming; Bao, Guangjun; Li, Yiping; Sun, Wangsheng; Li, Jing; Hong, Liang; Wang, Rui
- Abstract
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.
- Subjects
INDOLE compounds; ALUMINUM phthalocyanine; ENANTIOSELECTIVE catalysis; FRIEDEL-Crafts reaction; ALKYLATION
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 19, p5416
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201700494