Enantioselective Hydroarylation or Hydroalkenylation of Benzo[b]thiophene 1,1-Dioxides with Organoboranes

被引：10
|
作者：
Hu, Fangdong [1 ,2 ,3 ,4 ]
Jia, Jie [1 ,2 ,3 ]
Li, Ximing [1 ,2 ,3 ]
Xia, Ying [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Sch Publ Hlth, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Hosp 4, Chengdu 610041, Peoples R China
[3] Sichuan Univ, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
[4] Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 03期
关键词：
CATALYZED ASYMMETRIC 1,4-ADDITION; CHIRAL DIENE LIGANDS; QUATERNARY STEREOCENTERS; CONJUGATE ADDITION; KINETIC RESOLUTION; ARYLBORONIC ACIDS; ARYLATION; HYDROGENATION; CONSTRUCTION; SULFONES;
D O I：
10.1021/acs.orglett.0c04114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.
引用
收藏
页码：896 / 901
页数：6
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