Asymmetric Cascade Cyclization of Enynamides with Photogenerated Ketenes via Relay Gold and N-Oxide Catalysis

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成果类型：

期刊论文

作者：

Liu, Dan;Shu, Zhen-Cao;Zhang, Zhihan;Wang, Ze-Tian;Wang, Liang;...

通讯作者：

Lu, Liang-Qiu;Xiao, WJ;Xie, Ming-Sheng;Lu, LQ

作者机构：

[Lu, Liang-Qiu; Zhang, Zhihan; Liu, Dan; Xiao, Wen-Jing; Lu, LQ; Xiao, WJ] Cent China Normal Univ, Coll Chem, Engn Res Ctr Photoenergy Utilizat Pollut Control &, Minist Educ, Wuhan 430079, Peoples R China.

[Shu, Zhen-Cao] Wuhan Youji Ind Co Ltd, Wuhan 430082, Peoples R China.

[Wang, Ze-Tian; Wang, Liang] Jianghan Univ, Sch Chem & Environm Engn, Wuhan 430056, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ; Xie, Ming-Sheng; Xie, MS; Guo, Hai-Ming] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China.

[Xiao, Wen-Jing; Xiao, WJ] Wuhan Inst Photochem & Technol, Wuhan 430082, Peoples R China.

通讯机构：

[Lu, LQ ; Xie, MS] H

[Lu, LQ; Xiao, WJ ] C

Cent China Normal Univ, Coll Chem, Engn Res Ctr Photoenergy Utilizat Pollut Control &, Minist Educ, Wuhan 430079, Peoples R China.

Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China.

Wuhan Inst Photochem & Technol, Wuhan 430082, Peoples R China.

语种：

英文

关键词：

asymmetric cyclization;cascade reaction;gold catalysis;ketene;organocatalysis;visible light

期刊：

ACS CATALYSIS

ISSN：

2155-5435

年：

2024

卷：

期：

页码：

1741-1749

DOI：

10.1021/acscatal.3c05731

基金类别：

Central China Normal University [22271113, 21822103, 21820102003, 91956201, 21971056]; National Science Foundation of China; Central China Normal University

机构署名：

本校为第一且通讯机构

院系归属：

化学学院

摘要：

An asymmetric cascade cyclization of enynamides and alpha-diazoketones to produce chiral bicyclic lactams bearing chiral all-carbon quaternary stereocenters is realized with up to 95% yield, 98% ee, and >19:1 dr. The combination of visible light photoactivation and the relay of gold and N-oxide catalysis in a cascade process enabled the facile generation and controlled assembly of two reactive intermediates, ketene and aza-o-quinone methide. Theoretical calculations revealed a stepwise [4 + 2] cycloaddition mechanism, with the stereochemistry controlled by the amide group of the catalyst. Rema...

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Asymmetric Cascade Cyclization of Enynamides with Photogenerated Ketenes via Relay Gold and N-Oxide Catalysis

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