Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3+2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones

被引：5
|
作者：
Gil-Ordonez, Marta [1 ,2 ]
Maestro, Alicia [1 ,2 ]
Andres, Jose M. [1 ,2 ]
机构：
[1] Univ Valladolid, Fac Ciencias, GIR SintACat Inst Univ CINQUIMA, Valladolid 47011, Spain
[2] Univ Valladolid, Fac Ciencias, Dept Quim Organ, Valladolid 47011, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 11期
关键词：
ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PYRAZOLONE; TRANSFORMATIONS; CONSTRUCTION; ENALS;
D O I：
10.1021/acs.joc.3c00188
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The stereoselectivesynthesis of spirocyclic pyrazolin-5-ones byN-heterocyclic carbene (NHC) organocatalysis has been less studiedso far. For this reason and considering the interest of this classof compounds, here, we present the NHC-catalyzed [3 + 2]-asymmetricannulation of beta-bromoenals and 1H-pyrazol-4,5-dionesthat achieves to produce chiral spiropyrazolone-butenolides. The synthesisis general for aryl and heteroaryl beta-bromo-alpha,beta-unsaturatedaldehydes and 1,3-disubstituted pyrazolones. The spirobutenolideshave been obtained in good yields (up to 88%) and enantioselectivities(up to 97:3 er). This constitutes the first described example usingpyrazoldiones as the starting materials for this class of spiro compounds.
引用
收藏
页码：6890 / 6900
页数：11
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