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