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A simple and general method for the synthesis of a wide range of monocyclic 1,4‐azaborines, including the first examples containing B heteroatoms is described. Post‐heterocycle‐formation olefin isomerization was employed as a key strategy. This new synthetic method provides fundamental insight into the resonance stabilization and photophysical properties of 1,4‐azaborines.
Diels–Alder reactions employing 1,2‐azaborine heterocycles as 1,3‐dienes are reported. Carbocyclic compounds with high stereochemical and functional complexity are produced, as exemplified by the straightforward two‐step synthesis of an amino allyl boronic ester bearing four contiguous stereocenters as a single diastereomer. Whereas electron‐deficient dienophiles undergo irreversible Diels–Alder reactions,...
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