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

Eric J. Alexy; Tyler J. Fulton; Haiming Zhang; Brian M. Stoltz

doi:10.1039/C9SC01726G

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

Eric J. Alexy,

‡^a Tyler J. Fulton,

‡^a Haiming Zhang

*^b and Brian M. Stoltz

*^a

Author affiliations

* Corresponding authors

^a Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA
E-mail: stoltz@caltech.edu

^b Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA
E-mail: zhang.haiming@gene.com

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.

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DOI: https://doi.org/10.1039/C9SC01726G
Article type: Edge Article
Submitted: 08 Apr 2019
Accepted: 26 Apr 2019
First published: 17 May 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 5996-6000

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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, 10, 5996 DOI: 10.1039/C9SC01726G

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Chemical Science

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

Abstract

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

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