N-Heterocyclic Carbene (NHC)-Catalyzed/Lewis Acid Mediated Conjugate Umpolung of Alkynyl Aldehydes for the Synthesis of Butenolides: A Formal [3+2] Annulation

被引：55
|
作者：
Qi, Jing [1 ]
Xie, Xingang [1 ]
Han, Runfeng [1 ]
Ma, Donghui [1 ]
Yang, Juan [1 ]
She, Xuegong [1 ,2 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 13期
关键词：
allenolates; Lewis acids; N-heterocyclic carbenes; organocatalysis; umpolung; INTERMOLECULAR STETTER REACTION; CATALYZED HOMOENOLATE ADDITIONS; INTERNAL REDOX REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; EFFICIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; GAMMA-BUTYROLACTONES; COOPERATIVE CATALYSIS; NUCLEOPHILIC-ADDITION; ENALS;
D O I：
10.1002/chem.201204386
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reverse to success! A new formal [3+2] annulation reaction combining alkynyl aldehydes and β,Î-unsaturated α-ketoesters has been disclosed by using a NHC-catalyzed/Lewis acid mediated strategy. This cooperative catalysis strategy first allows the "allenolate" intermediate as a nucleophilic synthon at the β-position to react with activated electrophilic reagents by an addition reaction as the key C-C bond-forming step. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：4146 / 4150
页数：5
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