Tetrasubstituted Carbon Stereocenters via Copper-Catalyzed Asymmetric Sonogashira Coupling Reactions with Cyclic gem-Dihaloketones and Tertiary α-Carbonyl Bromides,ACS Catalysis

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Tetrasubstituted Carbon Stereocenters via Copper-Catalyzed Asymmetric Sonogashira Coupling Reactions with Cyclic gem-Dihaloketones and Tertiary α-Carbonyl Bromides
ACS Catalysis ( IF 11.3 ) Pub Date : 2022-08-01 , DOI: 10.1021/acscatal.2c01973
Xueling Mo ₁ , Han Huang ₂ , Guozhu Zhang _{1,

2}

Affiliation

The construction of chiral tetrasubstituted carbon stereocenters is an ongoing challenge in synthetic organic chemistry due to its prevalence in multiple disciplines. One efficient approach is the catalytic asymmetric C–C coupling reactions of a readily available racemic tertiary alkyl electrophile by simple organic nucleophiles. While a variety of secondary alkyl halides succeeded in asymmetric Cu-catalyzed Sonogashira-type cross-coupling reactions with diverse alkynes, tertiary alkyl halides have rarely been used in this kind of coupling reaction. Herein, we demonstrate that tertiary bromides can serve as efficient coupling partners in copper/bisoxazoline phenyl amine (BOPA)-catalyzed asymmetric alkynylation, leading to synthetically and medicinally valuable tertiary C–F stereocenters and all-carbon quaternary stereocenters.

中文翻译：

铜催化不对称 Sonogashira 偶联反应与环状偕二卤酮和叔 α-羰基溴化物的四取代碳立体中心

由于其在多个学科中的普遍存在，手性四取代碳立体中心的构建是合成有机化学中的一个持续挑战。一种有效的方法是通过简单的有机亲核试剂对容易获得的外消旋叔烷基亲电子试剂进行催化不对称 C-C 偶联反应。虽然多种仲卤代烷成功地与多种炔烃进行不对称铜催化的 Sonogashira 型交叉偶联反应，但叔卤代烷很少用于这种偶联反应。在此，我们证明叔溴化物可以作为铜/双恶唑啉苯胺 (BOPA) 催化的不对称炔基化的有效偶联伙伴，从而产生具有合成和药用价值的叔 C-F 立体中心和全碳四元立体中心。

更新日期：2022-08-01

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