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
Abstract
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
Files
nihms887325.pdf
Additional details
- PMCID
- PMC5555155
- Eprint ID
- 78510
- Resolver ID
- CaltechAUTHORS:20170623-095559709
- Israel Science Foundation
- 140/12
- Israel Academy of Sciences and Humanities
- Technion
- R01GM080269
- NIH
- DGE-1144469
- NSF Graduate Research Fellowship
- F32GM116304
- NIH Postdoctoral Fellowship
- Created
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2017-06-24Created from EPrint's datestamp field
- Updated
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2022-03-23Created from EPrint's last_modified field