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General Regio- and Diastereoselective Allylic C–H Oxygenation of Internal Alkenes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-06-26 , DOI: 10.1021/jacs.4c06421
Kyohei Yamada 1 , Kelvin Pak Shing Cheung 1 , Vladimir Gevorgyan 1
Affiliation  

Branched allylic esters and carboxylates are fundamental motifs prevalent in natural products and drug molecules. The direct allylic C–H oxygenation of internal alkenes represents one of the most straightforward approaches, bypassing the requirement for an allylic leaving group as in the classical Tsuji–Trost reaction. However, current methods suffer from limited scope─often accompanied by selectivity issues─thus hampering further development. Herein we report a photocatalytic platform as a general solution to these problems, enabling the coupling of diverse internal alkenes with carboxylic acids, alcohols, and other O-nucleophiles, typically in a highly regio- and diastereoselective manner.

中文翻译:


内部烯烃的一般区域和非对映选择性烯丙基 C-H 氧化



支链烯丙酯和羧酸酯是天然产物和药物分子中普遍存在的基本基序。内部烯烃的直接烯丙基 C-H 氧化代表了最直接的方法之一,绕过了经典 Tsuji-Trost 反应中对烯丙基离去基团的要求。然而,目前的方法范围有限(通常伴随着选择性问题),从而阻碍了进一步的发展。在此,我们报告了一种光催化平台作为这些问题的通用解决方案,能够将不同的内烯烃与羧酸、醇和其他O-亲核试剂偶联,通常以高度区域选择性和非对映选择性的方式。
更新日期:2024-06-26
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