Electronic effects in tautomeric equilibria: the case of chiral imines from d-glucamine and 2-hydroxyacetophenones?
Organic & Biomolecular Chemistry Pub Date: 2019-11-19 DOI: 10.1039/C9OB02147G
Abstract
A one-pot procedure for preparing a series of chiral imines by direct condensation of D-glucamine with 2-hydroxyacetophenones is described. Under conventional acetylation an unexpected mixture of two different peracetylated molecules is obtained, one with an open enamine structure, and the other incorporating an N-acetyl-1,3-oxazolidine into the acyclic skeleton. Surprisingly, both molecules coexist within the crystal's unit cell, as inferred from single-crystal X-ray analysis of a 5-bromo-substituted aryl derivative. Moreover, the 1,3-oxazolidine ring exists as rotational conformers (E,Z) owing to the restricted rotation around the N-acetyl bond. The equilibrium involving imine and enamine structures has been assessed in detail, providing in addition linear free-energy relationships between the tautomerization constants (KT) and the electronic effect of the substituents.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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