A Gold-Catalyzed Acid-Assisted Regioselective Cyclization for the Synthesis of Polysubstituted Oxazoles

被引：13
|
作者：
Wang, Qian [1 ]
Hoffmann, Stephanie [1 ]
Schiessl, Jasmin [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Hashmi, A. Stephen K. [1 ]
机构：
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 16期
关键词：
Alkynes; Gold; Carbenes; Oxazoles; Synthetic methods; ONE-POT SYNTHESIS; 2,5-DISUBSTITUTED OXAZOLES; ACCESS; ACTIVATION; NITRILES; CARBENES; ALCOHOLS; ALKENES; ALKYNES; ANTHRANILS;
D O I：
10.1002/ejoc.201900699
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Polysubstituted oxazole derivatives are obtained through a regioselective gold-catalyzed reaction of alpha-alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by alkyne oxidation with a pyridine N-oxide. Acidic conditions ensure that only one of the two carbonyl oxygen atoms in these intermediates selectively cyclizes to the products in excellent yields.
引用
收藏
页码：2384 / 2388
页数：5
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