N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones

被引：28

作者：

Kong, Xiangwen ^{[3
]}

Zhang, Guoxiang ^{[1
]}

Yang, Shuang ^{[2
]}

Liu, Xiaozhi ^{[3
]}

Fang, Xinqiang ^{[2
]}

机构：

[1] Fuzhou Univ, Coll Chem, Fuzhou 350116, Fujian, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China

[3] Liaoning Univ, Shenyang 110036, Liaoning, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 16期

关键词：

alkynyl 1,2-diketones; migration; N-heterocyclic carbenes; O-acylated allenolates; umpolung; BOND-FORMING REACTIONS; FORMAL 3+2 ANNULATION; ALPHA-PYRONES; ASYMMETRIC ORGANOCATALYSIS; GAMMA-BUTYROLACTONES; CONJUGATE UMPOLUNG; STETTER REACTION; NHC CATALYSIS; DERIVATIVES; REACTIVITY;

D O I：

10.1002/adsc.201700700

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The umpolung of alkynyl 1,2-diketones via N-heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important alpha-pyrones under very mild conditions. A completely new NHC-catalyzed umpolung pattern involving an O-acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products.

引用

页码：2729 / 2734

页数：6

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