Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules
Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules
复制标题
DOI：
10.1002/adsc.201500895
复制
发表时间：
2016-05-19
影响因子：
5.4
通讯作者：
Kleij, Arjan W.
中科院分区：
文献类型：
--
作者：
Guo, Wusheng;Laserna, Victor;Kleij, Arjan W.
氧杂环丁烷是药物相关合成中的通用结构单元，以诱导性质调节作用。尽管相关的环氧乙烷广泛用于与二氧化碳（CO2）的偶联化学中以提供增值的商品化学品，但氧杂环丁烷/CO2偶联仍然极其有限，尽管这些四元杂环的合成最近取得了进展。在这里，我们报告了一个有效的一锅三组分反应（3CR）的策略（取代）氧杂环丁烷，胺和CO2的偶联，以提供各种功能化的氨基甲酸酯具有良好的化学选择性和良好的产率。该过程是介导的铝基催化剂在相对温和的条件下，开发的催化方法可以应用于正式合成的两个药物相关的氨基甲酸酯与3CR是一个关键步骤。
Oxetanes are versatile building blocks in drug-related synthesis to induce property-modulating effects. Whereas related oxiranes are widely used in coupling chemistry with carbon dioxide (CO2) to afford value-added commodity chemicals, oxetane/CO2 couplings remain extremely limited despite the recent advances in the synthesis of these four-membered heterocycles. Here we report an effective one-pot three-component reaction (3CR) strategy for the coupling of (substituted) oxetanes, amines and CO2 to afford a variety of functionalized carbamates with excellent chemoselectivity and good yields. The process is mediated by an aluminium-based catalyst under relatively mild conditions and the developed catalytic methodology can be applied to the formal synthesis of two pharmaceutically relevant carbamates with the 3CR being a key step.