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Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates

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Abstract

The first enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates forming acyclic all-carbon quaternary stereocenters is reported. Excellent yields up to 99% and enantioselectivities up to 98% ee are obtained through the use of a new electron-deficient phosphinoxazoline (PHOX) ligand. Control of substrate enolate geometry is crucial for high selectivity. The obtained α-quaternary N-acyl indoles are formal ester equivalents, and represent a useful handle for further synthetic transformations.

Graphical abstract: Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates

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Publication details

The article was received on 08 Apr 2019, accepted on 26 Apr 2019 and first published on 17 May 2019


Article type: Edge Article
DOI: 10.1039/C9SC01726G
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates

    E. J. Alexy, T. J. Fulton, H. Zhang and Brian M. Stoltz, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC01726G

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