Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C-H Amidation for the Synthesis of Chiral Sulfoxides

Liu, Wentan1,2; Yang, Wu1,2; Zhu, Jiefeng1,2; Guo, Yonghong1,2; Wang, Na1,2; Ke, Jie1,2; Yu, Peiyuan1,2; He, Chuan1,2

2020-07-02

10.1021/acscatal.0c02109

ACS Catalysis   影响因子和分区

2155-5435

A rational designed Ir(III)-catalyzed enantioselective C-H amidation of dibenzyl sulfoxides through desymmetrization and parallel kinetic resolution is demonstrated. An Ir(III) complex equipped with a t-butyl cyclopentadienyl ligand and paired with a modified chiral proline enables the highly enantioselective sulfoxide-steered C-H bond activation, providing an efficient and straightforward way to construct sulfur chiral centers. A wide range of dibenzyl sulfoxides and dioxazolones are compatible with this process, giving access to a variety of highly functionalized sulfoxide compounds with synthetically attractive amide substitution groups in good yields and enantioselectivities. Moreover, the flexible derivatization of the amidated sulfoxide was elaborated, providing various types of chiral sulfoxide scaffolds that would be potentially useful in asymmetric catalysis as chiral bidentate and tridentate ligands.

enantioselective C-H functionalization chiral sulfoxides Iridium(III) catalysis dual-ligand effect desymmetrization and parallel kinetic resolution

SCI ; EI

英语

第一 ; 通讯

National Natural Science Foundation of China[21901104] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Physical

WOS:000547452800021

AMER CHEMICAL SOC

20202908952366

Catalysis ; Amides ; Chelation ; Ligands ; Iridium compounds ; Scaffolds

Construction Equipment:405.1 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China

Liu, Wentan,Yang, Wu,Zhu, Jiefeng,et al. Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C-H Amidation for the Synthesis of Chiral Sulfoxides[J]. ACS Catalysis,2020,10(13):7207-7215.

Liu, Wentan.,Yang, Wu.,Zhu, Jiefeng.,Guo, Yonghong.,Wang, Na.,...&He, Chuan.(2020).Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C-H Amidation for the Synthesis of Chiral Sulfoxides.ACS Catalysis,10(13),7207-7215.

Liu, Wentan,et al."Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C-H Amidation for the Synthesis of Chiral Sulfoxides".ACS Catalysis 10.13(2020):7207-7215.