A Full Regioselective and Stereoselective Synthesis of 4-Nitroisoxazolidines via Stepwise [3 + 2] Cycloaddition Reactions between (Z)-C-(9-Anthryl)-N-arylnitrones and (E)-3,3,3-Trichloro-1-nitroprop-1-ene: Comprehensive Experimental and Theoretical Study

In the contrast to all known [3 + 2] cycloadditions between nitrones and conjugated nitroalkenes, reactions of (E)-3,3,3-trichloro-1-nitroprop-1-ene with (Z)-C-(9-anthryl)-N-arylnitrones are proceeding in a fully regioselective and stereoselective manner. Additionally, density functional theory calculations suggest stepwise, zwitterionic mechanism of these cycloadditions.