Photo by satwikgawand from unsplash
A variety of oxazabicyclo[4.2.1]nonanone derivatives were prepared in good yields through a cinchonidine-catalyzed cascade reaction of N-aryl-α,β-unsaturated nitrones and 1-ethynylnaphthalen-2-ols. Mechanistic studies show that the reaction undergoes a [4 +… Click to show full abstract
A variety of oxazabicyclo[4.2.1]nonanone derivatives were prepared in good yields through a cinchonidine-catalyzed cascade reaction of N-aryl-α,β-unsaturated nitrones and 1-ethynylnaphthalen-2-ols. Mechanistic studies show that the reaction undergoes a [4 + 3] cycloaddition of nitrones to vinylidene o-quinone methide generated in situ from 1-ethynylnaphthalen-2-ols in the presence of cinchonidine, 1,3-rearrangement of N-O vinyl moieties, ring-opening, and finally double intramolecular cyclizations to afford oxazabicyclo[4.2.1]nonanones over five steps in a one-pot reaction.
Journal Title: Organic letters
Year Published: 2022
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!