Recent Advances in Azomethine Ylide Chemistry

Abstract

Publisher Summary Azomethine ylides are planar molecules composed of one nitrogen and two terminal sp2 carbons. At most, four geometrical isomers are possible for these transient molecules. Their cycloadditions to olefin or acetylene dipolarophiles give rise to the formation of two sets of carbon-carbon bonds in a single step. Because of the structural complexity of azomethine ylide itself compared to other dipoles and the stereochemical selectivity in the cycloadditions, a number of stereoisomers are possible for the cycloadducts. These two points make azomethine ylides one of the most attractive 1,3-dipoles, both in the fields of ylide chemistry and synthetic organic chemistry. Azomethine ylides can be classified in groups according to their structure. This chapter concentrates on the most basic ylides, acyclic azomethine ylides, in order to catch the generalized concepts involved in the azomethine ylide chemistry. Accordingly, it also deals with the recent advances of the chemistry of acyclic azomethine ylides covering its preparation, cycloadditions, intramolecular cycloadditions, and synthetic applications.