Enantioselective and Regiodivergent Nitroso Diels-Alder Reactions

Significance

Kinetic resolution is a well-known method to obtain enantioenriched compounds from racemates. In a parallel kinetic resolution, both enantiomers react to non-enantiomeric dia­stereomers. This methodology is applied to nitroso-Diels-Alder reactions where the racemic starting material is selectively converted into two out of eight possible diastereomers. Both diastereo­mers are obtained in high yield and ee. The products of the reaction can be further used in the synthesis of highly substituted chiral cyclohexanes.