Abstract
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, a reversible Diels-Alder reaction with the less electron-deficient methyl acrylate is observed. Both the N and the B substituent of the 1,2-azaborine exert significant influence on the [4+2] cycloaddition reactivity as well as the aromatic character of the heterocycle. The experimentally determined thermodynamic parameters of the reversible Diels-Alder reaction between 1,2-azaborines and methyl acrylate correlate with aromaticity trends and place 1,2-azaborines approximately between furan and thiophene on the aromaticity scale.
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