Published August 5, 2015
| Accepted Version + Supplemental Material
Journal Article
Open
Synthesis and exploration of electronically modified (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX in palladium-catalyzed enantio- and diastereoselective allylic alkylation: a practical alternative to (R)-(p-CF₃)₃-t-BuPHOX
- Creators
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Craig, Robert A., II
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Stoltz, Brian M.
Chicago
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Abstract
The synthesis of the novel electronically modified phosphinooxazoline (PHOX) ligand, (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX, is described. The utility of this PHOX ligand is explored in both enantio- and diastereoselective palladium-catalyzed allylic alkylations. These investigations prove (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX to be an effective and cost-efficient alternative to electronically modified PHOX ligands derived from the prohibitively expensive (R)-t-leucine.
Additional Information
© 2015 Elsevier Ltd. Received 27 May 2015, Accepted 10 June 2015, Available online 17 June 2015. The authors wish to thank the NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. R.A.C. gratefully acknowledges the support of this work provided by a fellowship from the National Cancer Institute of the National Institutes of Health under Award Number F31A17435.Attached Files
Accepted Version - nihms705028.pdf
Supplemental Material - mmc1.pdf
Files
nihms705028.pdf
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Additional details
- PMCID
- PMC4524747
- Eprint ID
- 58771
- Resolver ID
- CaltechAUTHORS:20150706-103427588
- NIH
- R01GM080269
- Amgen
- Caltech
- Gordon and Betty Moore Foundation
- NIH Predoctoral Fellowship
- F31A174359
- Created
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2015-07-06Created from EPrint's datestamp field
- Updated
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2022-06-01Created from EPrint's last_modified field