Catalytic Asymmetric Carbonylation of Prochiral Sulfonamides via C-H Desymmetrization

被引：46

作者：

Bai, Xing-Feng ^{[1
,2
,3
]}

Mu, Qiu-Chao ^{[1
,2
]}

Xu, Zheng ^{[3
]}

Yang, Ke-Fang ^{[3
]}

Li, Li ^{[3
]}

Zheng, Zhan-Jiang ^{[3
]}

Xia, Chun-Gu ^{[1
,2
]}

Xu, Li-Wen ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, SRI, LICP, Lanzhou 730000, Gansu, Peoples R China

[2] Univ Chinese Acad Sci, Lanzhou 730000, Gansu, Peoples R China

[3] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China

来源：

ACS CATALYSIS | 2019年 / 9卷 / 02期

基金：

中国国家自然科学基金;

关键词：

C-H activation; enantioselective carbonylation; lactam; desymmetrization; palladium; DFT; OXIDATIVE CARBONYLATION; ALIPHATIC-AMINES; ACTIVATION; IODINATION; BONDS;

D O I：

10.1021/acscatal.8b04725

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An enantioselective oxidative C-H/N-H carbonylation process was developed in this work. A bimetallic Pd/Cu-based catalyst system was found to catalyze enantioselective C(sp(2))-H carbonylation of prochiral arylsulfonamides via desymmetrization process in the presence of mono-N-protected amino acid ligands. This reaction provides a facile strategy to the stereoselective construction of the lactam-type products, such as isoindoline-1-ones and isoquinoline-l-ones, in good yields and enantioselectivities under balloon pressure with the mixture of CO/O-2. The reaction mechanism was rationalized by using density functional theory (DFT) study.

引用

页码：1431 / 1436

页数：11

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