LAUSR.org creates dashboard-style pages of related content for over 1.5 million academic articles. Sign Up to like articles & get recommendations!

Serendipitous one-pot synthesis of chiral dienes from pyranosidic 2,4-bistriflates.

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.

Keywords: synthesis chiral; pot synthesis; serendipitous one; dienes pyranosidic; chiral dienes; one pot

Journal Title: Carbohydrate research
Year Published: 2021

Link to full text (if available)


Share on Social Media:                               Sign Up to like & get
recommendations!

Related content

More Information              News              Social Media              Video              Recommended



                Click one of the above tabs to view related content.