Rhodium(I)-Catalyzed Direct Enantioselective C-H Functionalization of Indoles

Zhu, Dong-Xing1; Xu, Ming-Hua2,3,4

2023-02-01

10.1021/acs.joc.2c02624

JOURNAL OF ORGANIC CHEMISTRY   影响因子和分区

0022-3263

1520-6904

A highly regiospecific vinylogous carbene insertion protocol for direct asymmetric C-H functionalization of indoles with arylvinyldiazoacetates has been developed. Under the catalysis of simple Rh(I)/chiral diene complexes, the reaction occurs solely at the vinylogous position of the vinylcarbenoid with exceptional E selectivity and enantiocontrol. It provides an efficient way to obtain an interesting class of chiral indole scaffolds bearing an alpha,beta-unsaturated ester unit and a gem-diaryl carbon stereocenter in good yields (<99%) with excellent enantioselectivities (<96%) at room temperature.

SCI ; EI ; IC ; CCR

英语

通讯

National Natural Science Foundation of China["21971103","21672229"] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Shenzhen Science and Technology Innovation Commission[JCYJ20200109141408054]

Chemistry

Chemistry, Organic

WOS:000960615000001

AMER CHEMICAL SOC

20230613564820

Catalysis ; Enantioselectivity ; Olefins ; Scaffolds

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

CHEMISTRY

Web of Science

1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
4.Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

Zhu, Dong-Xing,Xu, Ming-Hua. Rhodium(I)-Catalyzed Direct Enantioselective C-H Functionalization of Indoles[J]. JOURNAL OF ORGANIC CHEMISTRY,2023,88(12):7844-7848.

Zhu, Dong-Xing,&Xu, Ming-Hua.(2023).Rhodium(I)-Catalyzed Direct Enantioselective C-H Functionalization of Indoles.JOURNAL OF ORGANIC CHEMISTRY,88(12),7844-7848.

Zhu, Dong-Xing,et al."Rhodium(I)-Catalyzed Direct Enantioselective C-H Functionalization of Indoles".JOURNAL OF ORGANIC CHEMISTRY 88.12(2023):7844-7848.