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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,...
Familienzusammenkunft: Eine allgemeine Synthesestrategie basierend auf nucleophiler Substitution liefert B‐substituierte 1,3‐Dihydro‐1,3‐azaborine (siehe Schema), die als BN‐Isostere von Arenen Potenzial für Anwendungen in der Biomedizin und den Materialwissenschaften haben. Strukturanalysen und Rechnungen besagen, dass der 1,3‐Dihydro‐1,3‐azaborin‐Heterocyclus hinsichtlich seiner Aromatizität eine...
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