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Oxazaborinines from Vinylogous N‑Allylic Amides: Reactivities of Underexplored Heterocyclic Building Blocks

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journal contribution
posted on 18.04.2018, 13:48 by Cedric L. Hugelshofer, Vignesh Palani, Richmond Sarpong
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.