Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology , Hangzhou 310014, China.
School of Material and Chemical Engineering, Chuzhou University , Chuzhou 239000, China.
Org Lett. 2018 Feb 16;20(4):913-916. doi: 10.1021/acs.orglett.7b03684. Epub 2018 Feb 2.
The successful development of the classical Pinnick oxidation into a new and promising oxidative lactonization reaction is reported. Chiral 3-oxindolepropionic aldehydes, Michael adducts of 3-olefinic oxindoles with aliphatic aldehydes, are directly converted to spirocyclic oxindole-γ-lactones solely by sodium chlorite via a tandem Pinnick oxidation/chlorination/substitution sequence. This reaction uses waste ClO generated in the initial Pinnick oxidation as an ecofriendly halogenating agent for the subsequent chlorination, and then it utilizes the byproduct OH formed in the chlorination to facilitate the final internal substitution.
报道了经典的 Pinnick 氧化反应成功发展为一种新的、有前途的氧化内酯化反应。手性 3-氧代吲哚丙酸醛是 3-烯烃吲哚与脂肪醛的迈克尔加成物，通过亚氯酸钠的串联 Pinnick 氧化/氯化/取代序列，直接转化为螺环吲哚-γ-内酰胺。该反应利用初始 Pinnick 氧化中生成的废 ClO 作为后续氯化的环保卤化剂，然后利用氯化中形成的副产物 OH 促进最终的内部取代。
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