Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates
Eric J. Alexy, Haiming Zhang* and Brian M. Stoltz*
*Genentech, Inc., 1 DNA Way, South San Francisco, California
94080; California Institute of Technology, Pasadena, California 91125, United
States, Email: zhang.haiming
gene.com, stoltzcaltech.edu
E. J. Alexy, H. Zhang, B. M. Stoltz, J. Am. Chem. Soc., 2018, 140, 10109-10112.
DOI: 10.1021/jacs.8b05560
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Abstract
An enantioselective Pd-catalyzed decarboxylative allylic alkylation of fully substituted acyclic enol carbonates provides linear α-quaternary ketones. The use of an electron-deficient phosphinooxazoline ligand renders the enolate geometry of the starting material inconsequential, with the same enantiomer of product obtained in the same level of selectivity regardless of the starting ratio of enolates.
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Key Words
ID: J48-Y2018
