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The wavelength-regulated stereodivergent synthesis of (Z)- and (E)-1,4-enediones from phosphonium ylides
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-09-06 , DOI: 10.1039/d1qo01085a
Mei Wang 1 , Yong-Qin He 2 , Yao Zhu 1 , Zhi-Bin Song 3 , Xiao-Yu Wang 1 , Hai-Yang Huang 1 , Ban-Peng Cao 1 , Wan-Fa Tian 1 , Qiang Xiao 1
Affiliation  

The wavelength-regulated, methylene blue organic dye catalyzed stereodivergent synthesis of (Z)- and (E)-1,4-enediones from stabilized phosphorous ylides is reported. Broad ranges of substrates and functional groups are tolerated. Mechanistic studies suggested singlet-oxygen-promoted (E)-alkene formation via a possible phospha-1,2-dioxetane intermediate, followed by a blue-LED triggered (E) → (Z) isomerization reaction.

中文翻译:

从鏻叶立德合成 (Z)- 和 (E)-1,4- 烯二酮的波长调节立体发散

报道了波长调节的亚甲基蓝有机染料催化的 ( Z )- 和 ( E )-1,4- 烯二酮从稳定的磷叶立德的立体发散合成。可以容忍广泛的底物和官能团。机理研究表明,单线态氧促进 ( E )-烯烃通过可能的phospha -1,2-二氧杂环丁烷中间体形成,然后是蓝色 LED 引发的 ( E ) → ( Z ) 异构化反应。
更新日期:2021-09-16
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