Abstract
Aldol reactions have played a central role in many stereoselective constructions of carbon-carbon bonds. During the past several years the selenocarbonyl group has been used both as a chiral interrogation tool (using {sup 77} SeNMR spectroscopy) and as a platform for the development of new chemical methods associated with selone based chiral derivatizing agents. During the course of these studies the authors have uncovered a new type of aldol reaction using chiral selone reagents in which the selenocarbonyl plays a pivotal role in determining the stereoselectivity of these reactions. This report describes the results of the studies involving the use of titanium(IV) enolates of N-acyl-oxaxolidin-2-selones with a variety of aldehydes.
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