Oxazaborinines from Vinylogous N-Allylic Amides: Reactivities of Underexplored Heterocyclic Building Blocks.
Cedric L HugelshoferVignesh PalaniRichmond SarpongPublished in: Organic letters (2018)
Access to a new class of oxazaborinines using an efficient transition-metal-catalyzed rearrangement is demonstrated. The method overcomes the synthetic challenge of achieving an aza-Claisen rearrangement of vinylogous N-allylic amide substrates, giving rise to a variety of highly modifiable oxazaborinine products. An investigation of the unique reactivity of these boron-based heterocycles has unveiled their underexplored potential as valuable building blocks and intermediates for organic synthesis.