Journal article
Dearomatized Alkylidene Dihydropyridines as Substrates for Mizoroki–Heck Cyclizations
ACS catalysis, Vol.6(7), pp.4465-4469
07/01/2016
DOI: 10.1021/acscatal.6b01151
Abstract
4-Substituted pyridines linked to iodoarene groups with alkyl amide tethers can be converted to the corresponding alkylidene dihydropyridines by treatment with ethyl chloroformate and Et3N. Subsequent exposure to Pd-catalyzed Mizoroki–Heck reaction conditions results in efficient intramolecular cyclization at the exocyclic alkene to afford isoindolinone and oxindole derivatives. Asymmetric construction of 3,3-disubstituted oxindoles and isoindolinones has also been achieved. This work demonstrates the ability to utilize reactive pyridine anhydrobases in metal-catalyzed transformations and provides the basis for design of new approaches to important heterocyclic ring systems.
Details
- Title: Subtitle
- Dearomatized Alkylidene Dihydropyridines as Substrates for Mizoroki–Heck Cyclizations
- Creators
- Madhur S JoshiF. Christopher Pigge
- Resource Type
- Journal article
- Publication Details
- ACS catalysis, Vol.6(7), pp.4465-4469
- Publisher
- American Chemical Society
- DOI
- 10.1021/acscatal.6b01151
- ISSN
- 2155-5435
- eISSN
- 2155-5435
- Grant note
- DOI: 10.13039/100000165, name: Division of Chemistry, award: CHE-1265488
- Language
- English
- Date published
- 07/01/2016
- Academic Unit
- Chemistry; Radiology
- Record Identifier
- 9983985882802771
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