Access to N-Substituted 2-Pyridones by Catalytic Intermolecular Dearomatization and 1,4-Acyl Transfer

被引：62

作者：

Xu, Guangyang ^{[1
]}

Chen, Ping ^{[2
]}

Liu, Pei ^{[1
]}

Tang, Shengbiao ^{[1
]}

Zhang, Xinhao ^{[2
]}

Sun, Jiangtao ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China

[2] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncoge, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 07期

关键词：

asymmetric catalysis; carbenes; dearomatization; diazo compounds; rearrangement; ASYMMETRIC DEAROMATIZATION; DIAZO-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; OXY-ALKYNYLATION; H BONDS; C-C; REARRANGEMENT; REGIO; DIRHODIUM(II); ALKYLATION;

D O I：

10.1002/anie.201812937

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel rhodium-catalyzed dearomatization of O-substituted pyridines to access N-substituted 2-pyridones has been developed. A computational study suggests a mechanism involving the formation of a pyridinium ylide followed by an unprecedented 1,4-acyl migratory rearrangement from O to C. Furthermore, the chiral dirhodium complexes serve as the catalyst for the asymmetric transformation with excellent enantioselective control. DFT calculations indicate the chirality is transferred from axial chirality to the central stereogenic centre. The stronger pi-pi interaction and CH-pi interaction account for the high enantioselectivity.

引用

页码：1980 / 1984

页数：5

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