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

Brian Stoltz, Nolan McDougal, Scott Virgil

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)1712-1716
Number of pages5
JournalSynlett
Volume2010
Issue number11
DOIs
StatePublished - Jun 14 2010
Externally publishedYes

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