Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

被引：123
|
作者：
Sahani, Rajkumar Lalji [1 ]
Liu, Rai-Shung [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 04期
关键词：
annulations; gold; heterocycles; reaction mechanisms; structure elucidation; NITRENE TRANSFER; CYCLOADDITIONS; YNAMIDES; PYRROLES; ALKYNES; BOND; N-SULFONYL-1,2,3-TRIAZOLES; CYCLOISOMERIZATION; REARRANGEMENT; 2H-AZIRINES;
D O I：
10.1002/anie.201610665
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.
引用
收藏
页码：1026 / 1030
页数：5
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