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2024 , Vol. 44 >Issue 12: 3739 - 3746

DOI: https://doi.org/10.6023/cjoc202405039

研究论文

有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应

  • 任岳 ,
  • 史望宇 ,
  • 唐义 ,
  • 郭红超
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  • 中国农业大学化学系 北京 100193

收稿日期: 2024-05-27

  修回日期: 2024-07-23

  网络出版日期: 2024-08-26

基金资助

国家自然科学基金(22071264)

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Phosphine-Catalyzed [5＋1] Annulation of Morita-Baylis-Hillman Carbonates with 1,3-Dicarbonyl Compounds

  • Yue Ren ,
  • Wangyu Shi ,
  • Yi Tang ,
  • Hongchao Guo
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  • Department of Chemistry, China Agricultural University, Beijing 100193
*Corresponding authors. E-mail:

Received date: 2024-05-27

  Revised date: 2024-07-23

  Online published: 2024-08-26

Supported by

National Natural Science Foundation of China(22071264)

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摘要

报道了有机膦催化的Morita-Baylis-Hillman (MBH)碳酸酯与1,3-二羰基化合物的[5＋1]环化反应, 以高产率和中等至优秀的非对映选择性得到一系列具有潜在生物活性的螺环己烯衍生物. 该环化反应是通过膦叶立德用双亲核试剂的连续1,6-共轭加成/亲核取代反应实现的.

关键词： 有机膦催化; Morita-Baylis-Hillman碳酸酯; 1,3-二羰基化合物; 双亲核试剂; 螺环己烯

本文引用格式

任岳 , 史望宇 , 唐义 , 郭红超 . 有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应[J]. 有机化学, 2024 , 44(12) : 3739 -3746 . DOI: 10.6023/cjoc202405039

Abstract

Phosphine-catalyzed [5＋1] annulation reaction of Morita-Baylis-Hillman (MBH) carbonates with 1,3-dicarbonyl compounds has been developed, producing biologically interesting spirocyclohexene derivatives in high yields with moderate to excellent diastereoselectivities. The annulation was achieved through sequential 1,6-conjugate addition/nucleophilic substu- tion reaction of phosphine ylides with dinucleophiles.

Key words： phosphine catalysis; Morita-Baylis-Hillman carbonate; 1,3-dicarbonyl compound; dinucleophile; spirocyclo- hexene

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