Contrasting Diastereoselectivity between Cyclic Nitrones and Azomethine Ylides. Stereocontrolled Pathways to <i>cis</i>-<i>anti</i>-<i>anti-cis</i>-Oxazatetraquinanes from a Bicyclic Nitrone
D. Srinivas Reddy, G. Sudhakar Reddy, Adilson Beatriz, E. J. Corey
Abstract
A study of [3 + 2] cycloaddition reactions of a bicyclic nitrone with various cyclopentenes has clarified the diastereomeric preferences as a function of the olefinic structure. It has also identified an important stereochemical difference between nitrones and the analogous azomethine ylides in [3 + 2] cycloaddition reactions.
Topics & Concepts
NitroneChemistryBicyclic moleculeCycloadditionDiastereomerStereochemistryOrganic chemistryCatalysisOrganic Chemistry Cycloaddition ReactionsAsymmetric Synthesis and CatalysisOxidative Organic Chemistry Reactions