Abstract
A rapid access to conformationally constrained γ-lactams
has been developed through the efficient RuO4 -mediated
oxidation of regioisomeric N -alkylisoxazolino-2-azanorbornane derivatives.
The competition between exocyclic and endocyclic oxidation on 2-azanorbornane
moieties can be driven by the proper choice of alkyl substituent
on the heterocyclic nitrogen atom. Valuable bridged γ-lactams - potential
analogues of classical β-lactam antibiotics - are
obtained by this method.
Key Words
ruthenium tetraoxide - lactams - 1,3-dipolar
cycloadditions - azanorbornenes
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