由硒介导的烯醇锂与一氧化碳的羰基化反应。
Carbonylation of lithium enolates with carbon monoxide mediated by selenium.
作者信息
Fujiwara Shin-ichi, Nishiyama Akira, Shin-ike Tsutomu, Kambe Nobuaki, Sonoda Noboru
机构信息
Department of Chemistry, Osaka Dental University, Hirakata, Osaka 573-1121, Japan.
出版信息
Org Lett. 2004 Feb 5;6(3):453-5. doi: 10.1021/ol036464u.
PMID:14748616
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.
摘要
[反应：见正文] 在温和条件下，酮和醛的烯醇锂盐在硒的作用下与一氧化碳发生羰基化反应，经烷基碘捕获后生成β-酮基和β-甲酰基硒醇酯。该反应通过一种独特的羰基化机理进行，该机理包括氧羰基化以及随后SeCO部分向α-碳的迁移。
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