A new mild method for the C-acylation of ketone enolates. A convenient synthesis of β-keto-esters, -thionoesters, and -thioesters

Karl J Hale; Milosz Grabski; Jakub T Flasz

doi:10.1021/ol303324a

A new mild method for the C-acylation of ketone enolates. A convenient synthesis of β-keto-esters, -thionoesters, and -thioesters

Org Lett. 2013 Jan 18;15(2):370-3. doi: 10.1021/ol303324a. Epub 2012 Dec 31.

Authors

Karl J Hale¹, Milosz Grabski, Jakub T Flasz

Affiliation

¹ The School of Chemistry and Chemical Engineering, and the CCRCB, Queen's University Belfast, Stranmillis Road, Belfast BT9 5AG, Northern Ireland, UK. k.j.hale@qub.ac.uk

PMID: 23276289
DOI: 10.1021/ol303324a

Abstract

A new method for ketone enolate C-acylation is described which utilizes alkyl pentafluorophenylcarbonates, thiocarbonates, and thionocarbonates as the reactive acylating agents, and MgBr(2)·Et(2)O, DMAP, and i-Pr(2)NEt as the reagents for enolization. A wide range of ketones have been observed to undergo clean C-acylation via this protocol.