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2019 , Vol. 39 >Issue 8: 2196 - 2202

DOI: https://doi.org/10.6023/cjoc201901040

研究论文

有机磷催化γ-甲基联烯酸酯[3+2]环化反应

  • 马蓉 ,
  • 宋格格 ,
  • 奚秋贞 ,
  • 杨柳 ,
  • 李二庆 ,
  • 段征
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  • 郑州大学化学与分子工程学院 国际磷化学实验室 河南省有机磷功能分子国际联合实验室 郑州 450001

收稿日期: 2019-01-25

  修回日期: 2019-03-22

  网络出版日期: 2019-04-09

基金资助

国家自然科学基金（Nos.21702189，21672193，21272218）、中国博士后基金会（Nos.2017M610458，2018T110737）和河南省博士后科研（No.001701006）资助项目.

收起

Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates

  • Ma Rong ,
  • Song Gege ,
  • Xi Qiuzhen ,
  • Yang Liu ,
  • Li Er-Qing ,
  • Duan Zheng
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  • International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received date: 2019-01-25

  Revised date: 2019-03-22

  Online published: 2019-04-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21702189, 21672193, 21272218), the China Postdoctoral Science Foundation (Nos. 2017M610458, 2018T110737) and the Postdoctoral Research Grant in Henan Province (No. 001701006).

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摘要

在有机磷催化下，γ-甲基联烯酸酯和烯基茚二酮经过[3+2]环加成反应，以中等到较好的产率、高化学选择性和非对映选择性形成一系列官能团化的螺环化合物.该反应具有操作简单、反应条件温和和底物适用性广等优点.需要指出的是，使用简单易得的PPh3作为催化剂，就能实现完全的α-区域选择性加成的环化产物.

关键词： 有机磷催化; γ-甲基联烯酸酯; [3+2]环化反应

本文引用格式

马蓉 , 宋格格 , 奚秋贞 , 杨柳 , 李二庆 , 段征 . 有机磷催化γ-甲基联烯酸酯[3+2]环化反应[J]. 有机化学, 2019 , 39(8) : 2196 -2202 . DOI: 10.6023/cjoc201901040

Abstract

The phosphine-catalyzed[3+2] annulation of γ-methyl allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is reported. In the reaction, a series of highly functionalized spiro[4.4]dec-6-ene skeletons were obtained in moderate to good yields and high diastereoselectivities. It should be noted that the perfect α-regioselective annulation adducts were obtained with simple PPh3 catalyst.

Key words： phosphine-catalyzed; γ-methyl allenoates; [3+2]annulation

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