Published April 27, 2016
| Accepted Version + Supplemental Material
Journal Article
Open
Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement
Abstract
A catalytic, enantioselective γ-alkylation of α,β-unsaturated malonates and ketoesters is reported. This strategy entails a highly regio- and enantioselective iridium-catalyzed α-alkylation of an extended enolate, and a subsequent translocation of chirality to the γ-position via a Cope rearrangement.
Additional Information
© 2016 American Chemical Society. Received: February 26, 2016. Published: April 7, 2016. We thank NIH-NIGMS (R01GM080269), the Gordon and Betty Moore Foundation, and Caltech for financial support. Shanghai Institute of Organic Chemistry (SIOC) is thanked for a postdoctoral fellowship to W.-B.L. Hiroshima International University is thanked for a postdoctoral fellowship to N.O. E.J.A. is grateful to the National Science Foundation for a predoctoral fellowship. K.T. acknowledges support from California HIV/AIDS Research Program (F08-CT-201). Mr. Lawrence Henlingand Dr. Michael Takase are acknowledged for X-ray analyses. We thank Dr. David VanderVelde for NMR expertise, and Dr. Mona Shahgholi and Naseem Torian for mass spectrometry assistance. The authors are also thankful to Professor Shu-Li You for the generous donation of N-aryl ligands and for helpful discussions.Attached Files
Accepted Version - nihms867687.pdf
Supplemental Material - ja6b02153_si_001.pdf
Supplemental Material - ja6b02153_si_002.pdf
Supplemental Material - ja6b02153_si_003.cif
Supplemental Material - ja6b02153_si_004.cif
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ja6b02153_si_001.pdf
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Additional details
- PMCID
- PMC5497580
- Eprint ID
- 66506
- DOI
- 10.1021/jacs.6b02153
- Resolver ID
- CaltechAUTHORS:20160427-092037065
- NIH
- R01GM080269
- Gordon and Betty Moore Foundation
- Caltech
- Shanghai Institute of Organic Chemistry (SIOC)
- Hiroshima International University
- NSF
- California HIV/AIDS Research Program
- F08-CT-201
- Created
-
2016-04-27Created from EPrint's datestamp field
- Updated
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2022-04-28Created from EPrint's last_modified field