Published September 11, 2017
| Version Supplemental Material + Accepted Version
Journal Article
Open
Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation
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1.
California Institute of Technology
Abstract
The first highly enantioselective iridium-catalyzed allylic alkylation providing access to products bearing an allylic all-carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one-pot preparation of α-quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored via a series of diverse product transformations.
Additional Information
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: July 10, 2017; Accepted manuscript online: July 19, 2017; Version of record online: August 9, 2017. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). Dr. Michael Takase, Dr. Lawrence Henling, and Niklas Thompson are acknowledged for assistance with X-ray analysis. Dr. Mona Shahgholi and Naseem Torian are thanked for mass spectrometry assistance. Dr. Scott Virgil is thanked for assistance with instrumentation. The authors declare no conflict of interest.Attached Files
Accepted Version - nihms915640.pdf
Supplemental Material - anie201707015-sup-0001-SI1.pdf
Files
anie201707015-sup-0001-SI1.pdf
Additional details
Additional titles
- Alternative title
- Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives via Iridium-Catalyzed Allylic Alkylation
Identifiers
- PMCID
- PMC5674796
- Eprint ID
- 79196
- DOI
- 10.1002/anie.201707015
- Resolver ID
- CaltechAUTHORS:20170719-091950600
Funding
- NIH
- R01GM080269
- Caltech
- Camille and Henry Dreyfus Foundation
- NIH Predoctoral Fellowship
- F31GM120804
Dates
- Created
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2017-07-19Created from EPrint's datestamp field
- Updated
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2022-03-23Created from EPrint's last_modified field