Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p‐Quinone Methides

Abstract

AbstractA diastereoselective [4+2] annulation reaction between in situ generated p‐quinone methides and isatin‐derived enoates has been developed. In the presence of manganese dioxide as an oxidant, a variety of tosylaminophenyl‐substituted p‐quinone methide intermediates can be readily generated in an in situ fashion. Without pre‐preparation of p‐QMs, this unprecedented cascade reaction proceeds efficiently under mild conditions, providing a straightforward route to synthesize 4‐phenyl‐substituted tetrahydroquinolines bearing 3,3’‐spirooxindole scaffolds in good yields.magnified image