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- Title
Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy.
- Authors
Wang, Ye; Zheng, Chao; You, Shu ‐ Li
- Abstract
A desymmetrization strategy was developed involving iridium-catalyzed allylic dearomatization of indoles. The six-membered-ring spiroindolenines contain three contiguous stereogenic centers, including an all-carbon quaternary center, and were obtained in up to 99 % yield with 99 % ee and >95:5 d.r. When treated with a catalytic amount of tosylic acid, six-membered spiroindolenine undergoes an unprecedented six-to-seven-membered ring expansion, affording the corresponding hexahydroazepino[4,5- b]indole.
- Subjects
IRIDIUM catalysts; CATALYTIC activity; INDOLE compounds; AROMATIC compounds; PHENOLS
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 47, p15289
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708419