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

被引：22

作者：

Hu, Linfeng ^{[1
]}

Li, Jinzhao ^{[1
]}

Zhang, Yongyan ^{[1
]}

Feng, Xiaoming ^{[1
]}

Liu, Xiaohua ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 14期

基金：

中国国家自然科学基金;

关键词：

SULFONIUM YLIDE FORMATION; ORGANIC-SYNTHESIS; RING EXPANSION; H INSERTION; STEVENS; LIGANDS; METAL; GUANIDINE; DIAZOESTERS; GENERATION;

D O I：

10.1039/d2sc00419d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective [1,2] Stevens rearrangement was realized by using chiral guanidine and copper(i) complexes. Bis-sulfuration of alpha-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.

引用

页码：4103 / 4108

页数：6

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