Your browser doesn't support javascript.
loading
Selectivity Switch in a Rhodium(II) Carbene Triggered Cyclopentannulation: Divergent Access to Three Polycyclic Indolines.
Liu, Hua-Kui; Wang, Sunewang R; Song, Xiang-Yang; Zhao, Liu-Peng; Wang, Lijia; Tang, Yong.
Afiliación
  • Liu HK; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
  • Wang SR; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
  • Song XY; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
  • Zhao LP; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
  • Wang L; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
  • Tang Y; The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Lu, Shanghai, 200032, China.
Angew Chem Int Ed Engl ; 58(13): 4345-4349, 2019 Mar 22.
Article en En | MEDLINE | ID: mdl-30791181
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.
Palabras clave
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China