Stereoselective Synthesis of Fully Substituted β-Lactams via Metal-Organo Relay Catalysis

被引：29

作者：

Chen, Long ^{[1
]}

Wang, Kai ^{[1
]}

Shao, Ying ^{[1
]}

Sun, Jiangtao ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 10期

基金：

中国国家自然科学基金;

关键词：

ENE-YNE-KETONES; TANDEM REACTION; CARBENE-TRANSFER; ZINC CARBENES; H INSERTION; ALKYNES; ACCESS; CARBONYLATION; ACTIVATION; GENERATION;

D O I：

10.1021/acs.orglett.9b01255

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel three-component reaction of N-hydroxyanilines, enynones, and diazo compounds has been developed via a metal-organo relay catalysis, providing highly functionalized beta-lactams containing two quaternary carbon centers in good yields and with excellent diastereoselectivities. This protocol features a sequential reaction of Rh-catalyzed imine formation, Wolff rearrangement, and benzoylquinine-catalyzed Staudinger cyclization using the stable, benign, and readily available N-hydroxyanilines as the N-resources.

引用

页码：3804 / 3807

页数：4

共 60 条

[1] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492

[2]

[Anonymous], ANGEW CHEM INT ED

[3] Catalytic Formal [4+2] Cycloadditions between Unactivated Allenes and N-Hydroxyaniline Catalyzed by AuCl3/CuCl2/O2 [J].

Chen, Jian-Ming ;

Chang, Chin-Jung ;

Ke, Yao-Jin ;

Liu, Rai-Shung .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) :4306-4311

[4] Donor- and acceptor-enynals/enynones [J].

Chen, Lianfen ;

Liu, Zhili ;

Zhu, Shifa .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (46) :8884-8898

[5] Transition-Metal-Catalyzed Intramolecular Nucleophilic Addition of Carbonyl Groups to Alkynes [J].

Chen, Lianfen ;

Chen, Kai ;

Zhu, Shifa .

CHEM, 2018, 4 (06) :1208-1262

[6] Organocatalytic Synthesis of Highly Substituted Furfuryl Alcohols and Amines [J].

Clark, J. Stephen ;

Boyer, Alistair ;

Aimon, Anthony ;

Garcia, Paloma Engel ;

Lindsay, David M. ;

Symington, Andrew D. F. ;

Danoy, Yves .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12128-12131

[7] The mechanism of the ketene-imine (Staudinger) reaction in its centennial:: Still an unsolved problem? [J].

Cossio, Fernando P. ;

Arrieta, Ana ;

Sierra, Miguel A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :925-936

[8] Anion Relay Enabled [3+3]-Annulation of Active Methylene Isocyanides and Ene-Yne-Ketones [J].

Dong, Jinhuan ;

Bao, Lan ;

Hu, Zhongyan ;

Ma, Shenghua ;

Zhou, Xinyi ;

Hao, Mengru ;

Li, Ni ;

Xu, Xianxiu .

ORGANIC LETTERS, 2018, 20 (04) :1244-1247

[9] Synthesis of Hindered α-Amino Carbonyls: Copper-Catalyzed Radical Addition with Nitroso Compounds [J].

Fisher, David J. ;

Burnett, G. Leslie ;

Velasco, Rocio ;

de Alaniz, Javier Read .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) :11614-11617

[10] Bifunctional lewis acid-nucleophile-based asymmetric catalysis:: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams [J].

France, S ;

Shah, MH ;

Weatherwax, A ;

Wack, H ;

Roth, JP ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1206-1215

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