Construction of Quaternary Allylic Amino Acid Derivatives through Palladium-Catalyzed Allylic Alkylation Reaction of Azlactones with Vinyl Aziridine

被引：1

作者：

Huang, Ke-Xin ^{[1
]}

Chen, Zhao-Yang ^{[1
]}

Liu, Xue-Guo ^{[1
]}

Ye, Hong-Yong ^{[1
]}

Gao, Wen-Chao ^{[2
]}

机构：

[1] Nanyang Inst Technol, Sch Biol & Chem Engn, Nanyang 473000, Henan, Peoples R China

[2] Nanyang Normal Univ, Sch Chem & Pharmaceut Engn, Nanyang 473000, Henan, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 20期

关键词：

allylic alkylation; quaternary allylic amino acid derivatives; Pd-catalyzed; vinyl aziridine; azlactones; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GAMMA-ADDITIONS; DESIGN; DIHYDROCOUMARINS; CYCLOADDITION; ACCESS; HETEROCYCLES; TERTIARY;

D O I：

10.1055/a-1878-8084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient Pd-catalyzed allylic alkylation reaction of azlactones with vinyl aziridine has been achieved for the first time to access functionalized quaternary allylic amino acid derivatives (17 examples, up to 89% yield and 80% ee). Moreover, the broad scope and easy transformations of the products reinforce the value of this approach, which can enrich the chemistry of quaternary allylic amino acid derivatives.

引用

页码：4495 / 4502

页数：8

共 57 条

[31] A Practical Aryl Unit for Azlactone Dynamic Kinetic Resolution: Orthogonally Protected Products and A Ligation-Inspired Coupling Process [J].

Tallon, Sean ;

Manoni, Francesco ;

Connon, Stephen J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) :813-817

[32] Chiral Bronsted Acid Catalyzed Stereoselective Addition of Azlactones to 3-Vinylindoles for Facile Access to Enantioenriched Tryptophan Derivatives [J].

Terada, Masahiro ;

Moriya, Kenichi ;

Kanomata, Kyohei ;

Sorimachi, Keiichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (52) :12586-12590

[33] Enantioselective Direct Aldol-Type Reaction of Azlactone via Protonation of Vinyl Ethers by a Chiral Bronsted Acid Catalyst [J].

Terada, Masahiro ;

Tanaka, Hiroyasu ;

Sorimachi, Keiichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) :3430-+

[34] Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl Aziridines with imido carboxylates [J].

Trost, Barry M. ;

Tandrick, Daniel R. ;

Brodmann, Tobias ;

Stiles, Dylan T. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (32) :6123-6125

[35] Enantioselective allylations of azlactones with unsymmetrical acyclic allyl esters [J].

Trost, BM ;

Ariza, X .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (46) :10727-10737

[36] Design of folded peptides [J].

Venkatraman, J ;

Shankaramma, SC ;

Balaram, P .

CHEMICAL REVIEWS, 2001, 101 (10) :3131-3152

[37] Bronsted Acid Catalyzed Dynamic Kinetic Resolution of Azlactones for the Synthesis of Aryl Glycine Derivatives [J].

Wang, Chao ;

Luo, Hong-Wen ;

Gong, Liu-Zhu .

SYNLETT, 2011, (07) :992-994

[38] Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives [J].

Wang, Tianli ;

Yu, Zhaoyuan ;

Hoon, Ding Long ;

Phee, Claire Yan ;

Lan, Yu ;

Lu, Yixin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :265-271

[39] Inverse-Electron-Demand Palladium-Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S-Ligand and Hydrogen Bonding [J].

Wang, Ya-Ni ;

Xiong, Qin ;

Lu, Liang-Qiu ;

Zhang, Qun-Liang ;

Wang, Ying ;

Lan, Yu ;

Xiao, Wen-Jing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) :11013-11017

[40] Hydrogen-Bond Directed Regioselective Pd-Catalyzed Asymmetric Allylic Alkylation: The Construction of Chiral α-Amino Acids with Vicinal Tertiary and Quaternary Stereocenters [J].

Wei, Xuan ;

Liu, Delong ;

An, Qianjin ;

Zhang, Wanbin .

ORGANIC LETTERS, 2015, 17 (23) :5768-5771

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