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Stereodefined rhodium-catalysed 1,4-H/D delivery for modular syntheses and deuterium integration
Nature Catalysis ( IF 37.8 ) Pub Date : 2021-07-08 , DOI: 10.1038/s41929-021-00643-9
Weiyi Wang 1 , Yibo Yu 1 , Bao Cheng 1 , Hui Qian 1 , Shengming Ma 1, 2 , Huayi Fang 3 , Xue Zhang 2
Affiliation  

Deuterium-incorporated compounds are of high interest owing to their importance in the pharmaceutical industry, organic synthesis and materials science. So far, the integration of deuterium into the inert, saturated magic methyl or methylene groups of covalent molecules remains challenging. Here, we present a 1,4-H delivery of allylic metallic species to provide a highly stereoselective and straightforward approach to 3-methyl-2(E)-enals or -enones from readily available 2,3-allenols and organoboronic acids. The reaction accommodates many synthetically versatile functional groups as well as multi-pharmacophores, and is not limited to the formation of 3-methyl derivatives. By applying 1,4-H or D delivery, deuterium atom(s) from differently deuterated allenols can be edited into the methyl or methylene groups of versatile organic skeletons, resulting in the efficient formation of 4-monodeuterated, 1,4- and 4,4-doubly deuterated, and 4,4,4-triply deuterated 2(E)-enals or -enones. These powerful platform molecules can provide straightforward paths to other deuterated compounds for different purposes.



中文翻译:

用于模块化合成和氘集成的立体铑催化 1,4-H/D 输送

掺入氘的化合物因其在制药工业、有机合成和材料科学中的重要性而备受关注。到目前为止,将氘整合到共价分子的惰性、饱和的神奇甲基或亚甲基中仍然具有挑战性。在这里,我们提出了烯丙基金属物质的 1,4-H 传递,为 3-甲基-2( E)-烯醛或-烯酮来自容易获得的 2,3-烯醇和有机硼酸。该反应包含许多合成通用的官能团以及多种药效团,并且不限于形成 3-甲基衍生物。通过应用 1,4-H 或 D 传递,来自不同氘化联烯醇的氘原子可以被编辑成多功能有机骨架的甲基或亚甲基,从而有效地形成 4-单氘化、1,4- 和 4 ,4-双氘代和 4,4,4-三重氘代 2( E )-烯醛或-烯酮。这些强大的平台分子可以为不同目的提供通往其他氘代化合物的直接途径。

更新日期:2021-07-08
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