High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates

Type
Article

Authors
Stoltz, Brian
McDougal, Nolan
Virgil, Scott

KAUST Grant Number
KUS-11- 006-02

Online Publication Date
2010-06-14

Print Publication Date
2010-07

Date
2010-06-14

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 non-polar 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.

Citation
Stoltz B, McDougal N, Virgil S (2010) High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates. Synlett 2010: 1712–1716. Available: http://dx.doi.org/10.1055/s-0030-1258094.

Acknowledgements
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.

Publisher
Georg Thieme Verlag KG

Journal
Synlett

DOI
10.1055/s-0030-1258094

PubMed ID
21072327

PubMed Central ID
PMC2976558

Permanent link to this record