Enantioselective [1,2]-Stevens rearrangement of thiosulfonates to construct dithio-substituted quaternary carbon centers,Chemical Science

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Enantioselective [1,2]-Stevens rearrangement of thiosulfonates to construct dithio-substituted quaternary carbon centers
Chemical Science ( IF 7.6 ) Pub Date : 2022-03-11 , DOI: 10.1039/d2sc00419d
Linfeng Hu ₁ , Jinzhao Li ₁ , Yongyan Zhang ₁ , Xiaoming Feng ₁ , Xiaohua Liu ₁

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An enantioselective [1,2] Stevens rearrangement was realized by using chiral guanidine and copper(I) complexes. Bis-sulfuration of α-diazocarbonyl compounds was developed through using thiosulfonates as the sulfenylating agent. It was undoubtedly an atom-economic process providing an efficient route to access novel chiral dithioketal derivatives, affording the corresponding products in good yields (up to 90% yield) and enantioselectivities (up to 96 : 4 er). A novel catalytic cycle was proposed to rationalize the reaction process and enantiocontrol.

中文翻译：

硫代磺酸盐的对映选择性 [1,2]-Stevens 重排构建二硫代取代的季碳中心

使用手性胍和铜 ( I ) 配合物实现了对映选择性 [1,2] Stevens 重排。通过使用硫代磺酸盐作为亚磺酰化剂，开发了 α-重氮羰基化合物的双硫化。毫无疑问，这是一种原子经济过程，为获得新型手性二硫缩酮衍生物提供了有效途径，以良好的产率（高达 90% 的产率）和对映选择性（高达 96 : 4 er）提供相应的产品。提出了一种新的催化循环来合理化反应过程和对映体控制。

更新日期：2022-03-11

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