Recent Advances in the Synthesis of Spiro-β-Lactams and Spiro-δ-Lactams

被引:39
作者
Alves, Nuno G. [1 ,2 ]
Alves, Americo J. S. [1 ,2 ]
Soares, Maria I. L. [1 ,2 ]
Pinho e Meloa, Teresa M. V. D. [1 ,2 ]
机构
[1] Univ Coimbra, Coimbra Chem Ctr, P-3004535 Coimbra, Portugal
[2] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal
关键词
beta-lactams; delta-lactams; spiro-beta-lactams; spiro-delta-lactams; penicillanates; spirocyclization; CARBAMOYL RADICAL GENERATION; KETENE-IMINE CYCLOADDITION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SPIROCYCLIC SCAFFOLDS; FACILE SYNTHESIS; ACCESS; ACIDS; PHOTOREACTIONS;
D O I
10.1002/adsc.202100013
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Spirocyclic molecules are widely recognized for their complex three-dimensional features and structural rigidity. Among this class of molecules, the spiro-lactams subclass stands out, being extensively explored due to its bioactivity and utility in a variety of scientific fields such as drug design and organic synthesis. Given the recognition of spirocyclic lactams' broad potential, several efforts have been engaged on the pursuit of new synthetic strategies towards these molecules. The present review gathers advances on the synthesis of both spiro-beta-lactams (spiroazetidin-2-ones) and spiro-delta-lactams (spiropiperidon-2-ones) reported since 2015. The work is divided into two distinct parts, each one dedicated to one of these types of spiro-lactam, with the approach used for building the spirocyclic system being extensively discussed, according to the method's scope, efficiency, selectivity, and reaction mechanism. 1. Introduction 2. Spiro-beta-Lactams 2.1. beta-Lactam Ring Synthesis 2.2. Non-beta-Lactam Ring Synthesis 2.3. beta-Lactam and Non-beta-Lactam Ring Synthesis 3. Spiro-delta-Lactams 3.1. delta-Lactam Ring Synthesis 3.2. Non-delta-Lactam Ring Synthesis 3.3. delta-Lactam and Non-delta-lactam Ring Synthesis 4. Conclusion
引用
收藏
页码:2464 / 2501
页数:38
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