Carbonylation of lithium enolates with carbon monoxide mediated by selenium.
[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.
Fujiwara
Shin-ichi
S
Department of Chemistry, Osaka Dental University, Hirakata, Osaka 573-1121, Japan. fujiwara@cc.osaka-dent.ac.jp
Nishiyama
Akira
A
Shin-ike
Tsutomu
T
Kambe
Nobuaki
N
Sonoda
Noboru
N