Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers,Organic Letters

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Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers
Organic Letters ( IF 4.9 ) Pub Date : 2021-12-06 , DOI: 10.1021/acs.orglett.1c03626
Arko Das ₁ , Harshit Joshi ₁ , Vinod K Singh ₁

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An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary–tertiary stereocenters is summarized. The chiral copper(I)–phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in α-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.

中文翻译：

2-烷基氮杂芳烃的不对称α-功能化：具有邻位立体中心的叔氟化物的合成

总结了一种合成含有邻位季-叔立体中心的氟化氮杂芳烃的对映选择性方法。手性铜 (I)-膦络合物与氮杂芳烃结合，然后迈克尔加成不饱和酰基咪唑，从而产生具有优异水平对映选择性（高达 99%）、非对映选择性（>20:1）和产量（高达 97%）。此外，还证明了酰基咪唑部分的后官能化。

更新日期：2021-12-17

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