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- Title
Selectivity Switch in a Rhodium(II) Carbene Triggered Cyclopentannulation: Divergent Access to Three Polycyclic Indolines.
- Authors
Liu, Hua‐Kui; Wang, Sunewang R.; Song, Xiang‐Yang; Zhao, Liu‐Peng; Wang, Lijia; Tang, Yong
- Abstract
A selectivity switch in a RhII/carbene‐triggered cyclopentannulation with catalytic InCl3 is reported for the first time, affording both diastereomers of the fused spiroindolines and an unusual bridged tetracyclic indoline in high yields with excellent selectivities. Mechanistic studies indicate an intramolecular annulation of the indole with an in situ formed aminocyclopropane. The stepwise thermal conversions from the kinetic spiroindoline to the metastable bridged indoline, and then to the thermodynamic spiroindoline, involving a ring‐opening rearrangement of a cyclopentane, is crucial for selectivity control.
- Subjects
RHODIUM isotopes; ANNULATION; POLYCYCLIC aromatic compounds; INDOLINE; CATALYTIC activity; INTRAMOLECULAR catalysis
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 13, p4389
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812294