钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应

doi:10.6023/cjoc202405020

有机化学

研究论文

钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应

朱波, 杨杨, 刘淇尹, 杜玮^*, 陈应春^*

四川大学华西药学院成都 610041

收稿日期:2024-05-15 修回日期:2024-06-21
基金资助:
国家自然科学基金(No. 21971166)资助项目.

Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

Zhu Bo, Yang Yang, Liu Qiyin, Du Wei^*, Chen Yingchun^*

West China School of Pharmacy, Sichuan University, Chengdu, 610041

Received:2024-05-15 Revised:2024-06-21
Contact: *E-mail: ycchen@scu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 21971166).

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摘要/Abstract

在醋酸钯和膦配体Synphos配合物的催化下, 从醛衍生的Morita-Baylis-Hillman (MBH)加成物碳酸酯可原位生成含π-烯丙基钯的1,4-全碳偶极子, 与1-氮杂二烯发生串联Michael加成/烯丙位取代反应,构建一系列含有三取代环外双键的八元氮杂环产物, 并取得了中等到良好的E/Z选择性和阻转选择性. 此外,在手性配体或者和手性季铵盐的协同催化下能够实现中等的对映选择性控制.

关键词: 钯/膦配合物, Morita-Baylis-Hillman碳酸酯, 全碳1,4-偶极子, (4+4)环化反应, 八元氮杂环

Here we report a (4 + 4) annulation reaction for the construction of medium-sized N-heterocycles. This process involves the generation of all-carbon 1,4-dipoles containing a π-allylpalladium complex from Morita-Baylis-Hillman (MBH) carbonates under the catalysis of Pd/Synphos, which then undergo Michael addition/N-allylic alkylation with 1-azadienes. A spectrum of eight-membered N-heterocycles featuring a trisubstituted exo-cyclic double bond are furnished efficiently, with moderate to good E/Z selectivity and moderate atroposelectivity. In addition, moderate enantioselectivity can be realized by using a chiral ligand or with the assistant of a chiral quaternary ammonium salt.

Key words: palladium/phosphine complex, Morita-Baylis-Hillman carbonates, all-carbon 1,4-dipoles, (4 + 4) annulation, eight-membered N-heterocycles

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朱波, 杨杨, 刘淇尹, 杜玮, 陈应春. 钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应[J]. 有机化学, doi: 10.6023/cjoc202405020.

Zhu Bo, Yang Yang, Liu Qiyin, Du Wei, Chen Yingchun. Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405020.

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钯/膦配合物催化Morita-Baylis-Hillman碳酸酯与氮杂二烯的(4 + 4)环化反应

Palladium/Phosphine Complex-Catalyzed (4 + 4) Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

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