有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1165-1172.DOI: 10.6023/cjoc201701043 上一篇    下一篇

研究论文

铑催化烯基氮杂环丙烷与炔胺的立体专一性[3+2]环加成反应(封面文章)

朱超泽, 冯见君, 张俊良   

  1. 华东师范大学化学与分子工程学院 上海 200062
  • 收稿日期:2017-01-21 修回日期:2017-02-16 发布日期:2017-02-20
  • 通讯作者: 冯见君,张俊良 E-mail:jjfeng@chem.ecnu.edu.cn;jlzhang@chem.ecnu.edu.cn
  • 基金资助:

    上海市扬帆计划(No.15YF1403600)和国家自然科学基金(Nos.21602062,21373088,21425205)资助项目.

Rhodium(Ⅰ)-Catalyzed Stereospecific [3+2] Cycloadditions of Vinylaziridines and Ynamides

Zhu Chaoze, Feng Jianjun, Zhang Junliang   

  1. School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
  • Received:2017-01-21 Revised:2017-02-16 Published:2017-02-20
  • Contact: 10.6023/cjoc201701043 E-mail:jjfeng@chem.ecnu.edu.cn;jlzhang@chem.ecnu.edu.cn
  • Supported by:

    Project supported by the Shanghai Sailing Program (No. 15YF1403600) and the National Natural Science Foundation of China (Nos. 21602062, 21373088, 21425205).

首次实现了铑催化的烯基氮杂环丙烷与炔胺底物的立体专一性的分子间[3+2]环加成反应.该反应具有较好的底物兼容性,反应条件温和,操作简便.此外,烯基氮杂环丙烷原料的手性可完全转移至环加成产物中,这为原子经济性且对映选择性地合成重要的2-氨基吡咯啉类衍生物提供了新的策略.

关键词: 过渡金属催化, 环加成反应, 烯基氮杂环丙烷, 炔胺, 含氮杂环

The first rhodium-catalyzed stereospecific intermolecular [3+2] cycloaddition reaction of vinylaziridines with ynamides was realized. The salient features of the transformation include broad substrate scope, mild reaction condition, and simple operation. Moreover, the chirality of vinylaziridines can be completely transferred to the cycloadducts, representing an atom-economic and enantiospecific protocol for the construction of valuable 2-amino pyrroline derivatives.

Key words: transition-metal catalysis, cycloaddition, vinylaziridine, ynamides, nitrogen heterocycles