Redox-Neutral α-C–H Functionalization of Pyrrolidin-3-ol,Organic Letters

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Redox-Neutral α-C–H Functionalization of Pyrrolidin-3-ol
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-24 00:00:00 , DOI: 10.1021/acs.orglett.7b03807
Cheng-Bo Yi ₁ , Zhi-Ying She ₁ , Yong-Feng Cheng ₁ , Jin Qu ₁

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A redox-neutral α-C–H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(−)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.

中文翻译：

Pyrrolidin-3-ol的氧化还原中性α-C–H官能化

市售吡咯烷-3-醇与单保护的对苯醌的氧化还原中性α-CH氧合生成N-芳基亚胺离子中间体，该中间体与硼酸亲核试剂原位反应生成一系列顺式-2-取代的吡咯烷-3-醇。通过这种策略，通过三个步骤从（3R，4R）-吡咯烷-3,4-二醇合成了8- epi -（-）-lentiginosine 。

更新日期：2018-01-24

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