Photo from archive.org
Attempted nucleophilic displacements of l-rhamnosyl 2,4-bistriflates led to serendipitous formation of a chiral diene via competing cascade eliminations. The reaction also followed the same pathway with d-rhamnosyl and d-mannosyl 2,4-bistriflates… Click to show full abstract
Attempted nucleophilic displacements of l-rhamnosyl 2,4-bistriflates led to serendipitous formation of a chiral diene via competing cascade eliminations. The reaction also followed the same pathway with d-rhamnosyl and d-mannosyl 2,4-bistriflates substrates providing access to dienes with opposite stereochemistry. The reaction presumably proceeds through E2 elimination of C2 triflate followed by allylic rearrangement. The easily accessible chiral dienes would be useful in the synthesis of natural products.
Journal Title: Carbohydrate research
Year Published: 2021
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!