Stereoselective Synthesis of C-Vinyl Glycosides via Nickel-Catalyzed Cross-Electrophile Couplings of 1,2-Glycosyl Orthoesters and Vinyl Halides

被引：3

作者：

Wang, Xin ^{[1
,2
,3
]}

Chen, Anrong ^{[3
]}

Zhao, Shiyin ^{[3
]}

Tao, Qiang ^{[2
,3
]}

Yang, Bo ^{[3
]}

Zhang, Xing ^{[2
]}

Zhu, Feng ^{[1
,3
]}

机构：

[1] Pingyuan Lab, Xinxiang 453007, Henan, Peoples R China

[2] Nanjing Normal Univ, Sch Food Sci & Pharmaceut Engn, Nanjing 210023, Jiangsu, Peoples R China

[3] Shanghai Jiao Tong Univ, China Frontiers Sci Ctr Transformat Mol FSCTM, Ctr Chem Glycobiol, Shanghai Key Lab Mol Engn Chiral Drugs,Sch Chem &, Shanghai 200240, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 23期

基金：

上海市自然科学基金; 中国国家自然科学基金; 国家重点研发计划;

关键词：

Glycosylation; Nickel catalysis; Cross-electrophile couplings; 1,2-Glycosyl orthoesters; C-C coupling; Stereochemistry; ARYL; OLIGOSACCHARIDE;

D O I：

10.1002/cjoc.202400651

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly stereoselective nickel-catalyzed cross-electrophile coupling of readily accessible, novel, stable oxygen-based glycosyl radical precursors, specifically 1,2-glycosyl orthoesters, is developed. This approach offers an effective pathway to synthesize diverse C-vinyl glycosides, characterized by good yields, excellent stereoselectivity, mild reaction conditions, a broad substrate scope, and versatile transformations of the resulting products.

引用

页码：3029 / 3034

页数：6

共 45 条

[1] Stereoselective Preparation of α-C-Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides
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ORGANIC LETTERS, 2018, 20 (24) : 7991 - 7995
[2] Nickel-catalyzed cross-electrophile coupling reactions of vinyl halides
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Weix, Daniel
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[3] Nickel-catalyzed cross-electrophile couplings of aryl fluorosulfates with vinyl chlorosilanes
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Du, Hong-Jian
Jing, Jia-Wen
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[4] Nickel-Catalyzed Cross-Electrophile Vinyl-Vinyl Coupling: An Approach to Structurally Versatile Dienylboronates
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[5] Preparation of glycosyl carboxylic acids via stereoselective synthesis and oxidative cleavage of C-vinyl glycosides
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[6] Expansion of scope for nickel-catalyzed cross-electrophile couplings of sulfonamides for cyclopropane synthesis
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Castro, Anthony
Lucas, Erika
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[7] Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
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Li, Changfeng
Yang, Sihang
Pedro, Dylan
Weix, Daniel J.
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[8] Amide and peptide synthesis via nickel-catalyzed cross-electrophile coupling
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[9] Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling
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[10] Synthesis of C-vinyl glycosides via Pd(0)-catalyzed cyclization
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Nolen, Ernest G.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247

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