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Published July 19, 2017 | Supplemental Material + Accepted Version
Journal Article Open

Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully-Substituted Amide Enolates


We report a divergent and modular protocol for the preparation of acyclic molecular frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand.

Additional Information

© 2017 American Chemical Society. Received: April 22, 2017; Published: June 19, 2017. This research was supported by the Israel Science Foundation administrated by the Israel Academy of Sciences and Humanities (140/12), the Fund for Promotion of Research at the Technion, the NIH-NIGMS (R01GM080269), and the NSF (predoctoral research fellowship to D.C.D., No. DGE-1144469). Research reported in this publication was supported by the NIH-NIGMS under Award Number F32GM116304 (postdoctoral fellowship to J.T.M.). I.M. is holder of the Sir Michael and Lady Sobell Academic Chair (Technion). Dr. Mona Shahgholi (Caltech) and Naseem Torian (Caltech) are thanked for mass spectrometry assistance. Dr. Scott Virgil (Caltech) is thanked for instrumentation assistance and helpful discussions. The authors declare no competing financial interest.

Attached Files

Accepted Version - jacs_2E7b04086.pdf

Accepted Version - nihms887325.pdf

Supplemental Material - ja7b04086_si_001.pdf


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August 19, 2023
October 26, 2023