Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII /PV Hybrid Ylides

被引：1

作者：

Ye, Xingchen ^{[1
]}

Wang, Zhaofeng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

来源：

SYNLETT | 2024年 / 35卷 / 10期

基金：

中国国家自然科学基金;

关键词：

oxazoles; copper catalysis; carbenoids; 3+2] annulation; cascade reaction; amides; C-H ARYLATION; ONE-POT SYNTHESIS; 2,5-DISUBSTITUTED OXAZOLES; IODONIUM YLIDES; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED OXAZOLES; CARBENE PRECURSORS; 2+2+1 ANNULATION; ALKYNES; ROUTE;

D O I：

10.1055/a-2185-0673

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a novel and efficient method for oxazole synthesis through a copper-catalyzed [3+2] annulation/olefination cascade between readily available iodonium-phosphonium hybrid ylides and amides. An unprecedented alpha-phosphonium Cu carbenoid acts as the key intermediate. This method features excellent regioselectivity with mild reaction conditions and a broad substrate scope. Its synthetic utility is demonstrated by its application in late-stage functionalizations and the rapid synthesis of a chiral ligand based on an oxazole motif.

引用

页码：1153 / 1159

页数：7

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