Synthesis of Functionalized Bicyclic Imines via Intramolecular Azide‐Alkene 1,3‐Dipolar Cycloaddition/Intramolecular Stork Alkylation Cascade Reaction

Abstract

A cascade intramolecular azide‐alkene 1,3‐dipolar cycloaddition/Stork alkylation reaction has been developed for the synthesis of functionalized cyclic imines with a pyrroline and piperideine structures, employing readily available ω‐azidodienes.

Intramolecular Cycloaddition Reactions of cis-1,2-Dihydrocatechol Derivatives Incorporating C3-Tethered Diazoketones, Nitrile Oxides, and Azides: Stereocontrolled Routes to Enantiomerically Pure Spiro[5.5]undecanes and Related Systems

“…The intramolecular addition of a pendant azide to the cis -1,2-dihydrocatechol moiety was the final process to be examined as part of the present study . The substrate used for this purpose was prepared by the straightforward pathway shown in Scheme .…”