Recent Advances in Azlactone Transformations

被引:76
作者
Marra, Isabella F. S. [1 ]
de Castro, Pedro P. [1 ]
Amarante, Giovanni W. [1 ]
机构
[1] Univ Fed Juiz de Fora, Dept Chem, Sao Pedro, Juiz De Fora, Brazil
关键词
Azlactones; Oxazolones; Catalysis; Erlenmeyer; MANNICH-TYPE REACTION; DIASTEREOSELECTIVE SYNTHESIS; ARYLIDENE AZLACTONES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ACID-DERIVATIVES; CYCLOADDITION; CONSTRUCTION; COMBINATION; CATALYSIS;
D O I
10.1002/ejoc.201901076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azlactones, also known as oxazolones, are versatile building blocks in organic synthesis due to the presence of multiple pro-nucleophilic and electrophilic reactive sites. Recently, several elegant organo- and metal-catalyzed studies have been described, allowing the stereocontrolled access to complex structures in only one or a few chemical steps. Moreover, the development of one-pot, tandem and domino reactions greatly enhanced the azlactone scaffold potential. In this context, this review aims to cover novel methodologies, including a brief overview of oxazolones and Erlenmeyer azlactones preparation. New approaches towards classical reactions, such as dynamic kinetic resolution, cycloadditions, and conjugate additions will be presented as well as new methodologies involving photochemical and flow chemistry technology. Finally, for most studies, selected examples will be presented and mechanistic pathways and/or activating modes will be carefully discussed.
引用
收藏
页码:5830 / 5855
页数:26
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