Carbonylation of lithium enolates with carbon monoxide mediated by selenium

Org Lett. 2004 Feb 5;6(3):453-5. doi: 10.1021/ol036464u.

Abstract

[reaction: see text] Lithium enolates of ketones and aldehydes undergo carbonylation with carbon monoxide with the aid of selenium under mild conditions to yield beta-keto and beta-formyl selenol esters after trapping with alkyl iodides. This reaction proceeds via a unique carbonylation mechanism comprised of O-carbonylation and subsequent migration of the SeCO moiety to the alpha-carbon.