Mechanistic Aspects of the Ketene-Imine Cycloaddition Reactions

Author(s): Alessandro Venturini, Javier Gonzalez

Journal Name: Mini-Reviews in Organic Chemistry

Volume 3 , Issue 3 , 2006

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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 β-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.

Keywords: β -Lactams, ketene, imine, Staudinger reaction, ketene-imine cycloaddition, ab initio calculations

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Article Details

Year: 2006
Page: [185 - 194]
Pages: 10
DOI: 10.2174/1570193X10603030185
Price: $65

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