Published July 2010
| Published + Accepted Version
Journal Article
Open
High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
Chicago
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Abstract
The use of high-throughput screening allowed for the optimization of reaction conditions for the palladium-catalyzed asymmetric decarboxylative alkylation reaction of enolate-stabilized enol carbonates. Changing to a nonpolar reaction solvent and to an electron-deficient PHOX derivative as ligand from our standard reaction conditions improved the enantioselectivity for the alkylation of a ketal-protected,1,3-diketone-derived enol carbonate from 28% ee to 84% ee. Similar improvements in enantioselectivity were seen for a β-keto ester derived and an α-phenyl cyclohexanone-derived enol carbonate.
Additional Information
© 2010 Thieme Stuttgart. Received 7 April 2010. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support.Attached Files
Published - McDougal2010p10624Synlett.pdf
Accepted Version - nihms243552.pdf
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Additional details
- PMCID
- PMC2976558
- Eprint ID
- 19033
- Resolver ID
- CaltechAUTHORS:20100713-135750673
- King Abdullah University of Science and Technology (KAUST)
- KUS-11- 006-02
- NIH
- R01GM080269-01
- Abbott Laboratories
- Amgen
- Gordon and Betty Moore Foundation
- Caltech
- Created
-
2010-08-04Created from EPrint's datestamp field
- Updated
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2021-11-08Created from EPrint's last_modified field