One-Pot Synthesis of Bicyclic Isoxazolidines with Five Stereogenic Centers

Significance

An asymmetric one-pot synthesis of bicyclic isoxazolidines through a domino process involving a Michael addition-in situ condensation-intramolecular nitrone [2+3] cycloaddition sequence using catalyst 1 is reported. A wide range of nitroalkenes was tested giving good yields with high diastereo- and enantioselectivities. Applying 6-alkenylaldehyde in this synthesis to afford a [4,3,0]-isoxazolidine derivative gave similarly good results and notably only the exo product was formed.