3,4-Dihydroxypyrrolidines via modified tandem aza-Payne/hydroamination pathway.
3,4-Dihydroxypyrrolidines via modified tandem aza-Payne/hydroamination pathway.
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DOI：
10.1021/ol301204w
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发表时间：
2012-06
期刊：
影响因子：
5.2
通讯作者：
Aman Kulshrestha;Nastaran Salehi Marzijarani;Kumar Dilip Ashtekar;R. Staples;B. Borhan
中科院分区：
文献类型：
--
作者：
Aman Kulshrestha;Nastaran Salehi Marzijarani;Kumar Dilip Ashtekar;R. Staples;B. Borhan
串联aza-Payne/氢胺化反应的结果通过使用潜在亲核试剂进行修饰。后者最初作为亲电试剂拦截氮化吡啶烷氧化物，随后变成亲核试剂，从而执行氮化吡啶环打开，与分子内的aza-Payne途径竞争。随后在同一锅中进行氢胺化反应，得到N-Ts酰胺碳酸盐，它可以很容易地转化为具有生物意义的3,4-二羟基内酯。
The outcome of a tandem aza-Payne/hydroamination reaction is modified via the use of a latent nucleophile. The latter initially serves as an electrophile to intercept the aziridine alkoxide and afterward turns into a nucleophile thereby performing the aziridine ring opening, out competing the intramolecular aza-Payne pathway. Subsequent hydroamination in the same pot provides N-Ts enamide carbonates, which can be easily converted into biologically significant 3,4-dihydroxylactams.