Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis
Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis
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DOI：
10.1021/acs.orglett.9b04034
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发表时间：
2020-01-17
期刊：
影响因子：
5.2
通讯作者：
Berkessel, Albrecht
中科院分区：
文献类型：
--
作者：
Harnying, Wacharee;Neudoerfl, Joerg-M.;Berkessel, Albrecht
本文报道了一种高效的NHC催化氧化8-氧代香茅醛和8-氧代香茅醛一步合成荆芥内酯的方法。合成了几种新的、“易于制备”的N-Mes-或N-Dipp-取代的1，2，4-三唑盐，并将其与碱和化学计量的有机氧化剂组合用作预催化剂。在优化的条件下，NLs在温和的条件下以非常好的产率和非对映体纯获得。所用氧化剂可在操作简单的条件下回收和循环使用。
An efficient oxidative NHC-catalyzed one-step transformation of (S)- or (R)-8-oxocitronellal to nepetalactone (NL) in enantio- and diastereomerically pure form has been developed. Several new and "easy to make" N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.