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- Title
Organocatalytic Asymmetric Arylative Dearomatization of 2,3-Disubstituted Indoles Enabled by Tandem Reactions.
- Authors
Zhang, Yu-Chen; Zhao, Jia-Jia; Jiang, Fei; Sun, Si-Bing; Shi, Feng
- Abstract
The organocatalytic asymmetric arylative dearomatization of indoles was achieved through two tandem approaches involving 2,3-disubstituted indoles and quinone imine ketals. One approach utilized the enantioselective cascade 1,4 addition/alcohol elimination reaction, the other employed the one-pot tandem arylative dearomatization/transfer hydrogenation sequence. In both cases, enantiomerically pure indole derivatives that bear an all-carbon quaternary stereogenic center were generated in high yields and excellent stereoselectivities (all d.r.>95:5, up to 99 % ee).
- Subjects
AROMATIZATION catalysts; ORGANOCATALYSIS; ASYMMETRIC synthesis; STEREOSELECTIVE reactions; INDOLE; HETEROCYCLIC compounds synthesis; HYDROGENATION; SUBSTITUENTS (Chemistry)
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 50, p14132
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201408551