Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2461-2468.DOI: 10.6023/cjoc202411023 Previous Articles     Next Articles

ARTICLES

Brønsted酸催化α-烯丙基-1,3-二酮的逆Claisen反应

王亮霞, 徐长明*()   

  1. 兰州交通大学化学化工学院 兰州 730070
  • 收稿日期:2025-01-03 修回日期:2025-01-23 发布日期:2025-02-27
  • 通讯作者: 徐长明
  • 基金资助:
    国家自然科学基金(22061025); 甘肃省自然科学基金(20JR10RA220); 兰州交通大学“百人计划”基金资助项目

Retro-Claisen Reaction of α-Allyl-1,3-diketones Catalyzed by Brønsted Acid

Liangxia Wang, Changming Xu*()   

  1. School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou 730070
  • Received:2025-01-03 Revised:2025-01-23 Published:2025-02-27
  • Contact: Changming Xu
  • Supported by:
    National Natural Science Foundation of China(22061025); Natural Science Foundation of Gansu Province(20JR10RA220); Foundation of a Hundred Youth Talents Training Program of Lanzhou Jiaotong University

Brønsted acid catalyzed retro-Claisen reaction of α-allyl-1,3-diketones with H2O was reported, giving a series of ketoester compounds with moderate yield, which provided a new method for the synthesis of γ-hydroxy ketones. This reaction features transition metal-free, mild reaction conditions and simple operation, and represents a novel retro-Claisen reaction pathway. The 18O isotope labeling experiment confirmed that the oxygen atom in the hydroxyl group of γ-hydroxy ketone came from water.

Key words: retro-Claisen reaction, α-allyl-1,3-diketone, Brønsted-acid, hemiketal