Published January 23, 2020
| Version Accepted Version + Supplemental Material
Journal Article
Open
Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates
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1.
California Institute of Technology
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2.
Roche (United States)
Abstract
The enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted α-hydroxy acyclic enol carbonates providing tetrasubstituted benzoin derivatives is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochemically rich derivatives.
Additional Information
© 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. Issue Online: 23 January 2020; Version of Record online: 26 November 2019; Accepted manuscript online: 05 November 2019; Manuscript revised: 02 November 2019; Manuscript received: 03 October 2019. We thank NIH-NIGMS (R01GM080269) and Caltech for financial support. E.J.A. thanks the National Science Foundation for a predoctoral fellowship. Larry Henling and Dr. Michael Takase are thanked for X-ray crystallographic structure determination. We thank Dr. David VanderVelde for NMR expertise and Dr. Scott Virgil for instrumentation and SFC assistance.Attached Files
Accepted Version - Lavernhe_et_al-2019-Advanced_Synthesis___Catalysis.pdf
Accepted Version - nihms-1643083.pdf
Supplemental Material - adsc201901281-s1-si_1.pdf
Supplemental Material - adsc201901281-s2-si_2.cif
Files
adsc201901281-s1-si_1.pdf
Additional details
Identifiers
- PMCID
- PMC7942817
- Eprint ID
- 99689
- Resolver ID
- CaltechAUTHORS:20191106-101057290
Funding
- NIH
- R01GM080269
- Caltech
- NSF Predoctoral Fellowship
Dates
- Created
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2019-11-06Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field