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Access to Spiroindolines and Spirodihydrobenzofurans via Pd-Catalyzed Domino Heck Spiroyclization through C–H Activation and Carbene Insertion

Author:
Liu, Jian-Guo, Chen, Wen-Wen, Gu, Chang-Xue, Xu, Bin, Xu, Ming-Hua
Source:
Organic letters 2018 v.20 no.9 pp. 2728-2732
ISSN:
1523-7052
Subject:
carbenes, carbon, carbon-hydrogen bond activation, catalytic activity, chemical reactions, chemical structure, ligands, palladium
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.
Agid:
6083919