The [2+2]-cycloaddition reaction of imines with ketenes, also known as Staudinger reaction, is one of the most commonly employed synthetic entries to the ?-lactam ring. Despite this, the detailed mechanism of this reaction has remained an open debate for many years. However, the application of theoretical methods has allowed a deeper understanding of many intricacies surrounding the Staudinger reaction. The experimental evidence and the theoretical studies carried out on the Staudinger reaction mechanism, using ab initio and Density-functional theory methods, are reviewed. Special emphasis is placed on the competition between the concerted and stepwise reaction pathways and the origin of the stereoselectivity of the reaction.
Mechanistic Aspects of the Ketene-Imine Cycloaddition Reactions
VENTURINI ALESSANDRO;
2006
Abstract
The [2+2]-cycloaddition reaction of imines with ketenes, also known as Staudinger reaction, is one of the most commonly employed synthetic entries to the ?-lactam ring. Despite this, the detailed mechanism of this reaction has remained an open debate for many years. However, the application of theoretical methods has allowed a deeper understanding of many intricacies surrounding the Staudinger reaction. The experimental evidence and the theoretical studies carried out on the Staudinger reaction mechanism, using ab initio and Density-functional theory methods, are reviewed. Special emphasis is placed on the competition between the concerted and stepwise reaction pathways and the origin of the stereoselectivity of the reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
