Thermal Intramolecular [2+2] Cycloaddition: Synthesis of 3‐Azabicyclo[3.1.1]heptanes from Morita–Baylis–Hillman Adduct‐Derived 4,4‐Diaryl‐1,3‐dienes

Abstract

AbstractVarious 3‐azabicyclo[3.1.1]heptane derivatives were synthesized from Morita–Baylis–Hillman adduct‐derived 1,3‐dienes bearing a 4,4‐diaryl moiety through a thermal intramolecular [2+2] cycloaddition approach. By using the same approach, bicyclo[3.1.1]heptane, 3‐azabicyclo[3.2.0]heptane, and 3‐oxabicyclo[3.1.1]heptane derivatives could also be synthesized. A structurally similar dimethylallyl derivative underwent an intramolecular ene reaction to afford the pyrrolidine derivative.magnified image