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Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C–H Activation and Carbene Insertion
- Source :
- Organic Letters. 20:2728-2732
- Publication Year :
- 2018
- Publisher :
- American Chemical Society (ACS), 2018.
-
Abstract
- A new palladium-catalyzed domino approach for the synthesis of attractive spirocyclic indolines and dihydrobenzofurans was developed. The reaction proceeds through a sequential intramolecular Heck spirocyclization, remote C-H activation, and diazocarbonyl carbene insertion. Various spiroindolines and spirodihydrobenzofurans containing two quartenary carbon stereocenters were readily obtained in good to excellent yields. A preliminary study of asymmetric spirocyclization using chiral monophosphoramidite as a ligand was also conducted, enabling access to highly valuable chiral spiroindolines with up to 80% ee.
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 20
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....34f08da1084323c2121baa454a2b74b8