Abstract
The reactions of the morpholino enamine of 2-norbornanone towards a series of cyclic and acyclic conjugated nitroolefins resulted in the formation of the corresponding 1,2-oxazine N- oxides through an exo approach of the electrophiles. The stability of the heterocycles was strongly influenced by the nature of the substituents and in some cases it has been found to be unexpectedly high. Differently from analogous systems, opening of the heterocyclic ring to the corresponding enamine systems was not observed.
Highlights
The versatility of the conjugated nitroalkenes as synthetic tools in their reactions with nucleophilic olefins is known.[1,2,3,4,5,6,7,8,9] In the particular case in which the reacting centres are prochiral, the approach of the two reactants can be either like or unlike[8] and the first step involves the diastereoselective formation of a new carbon-carbon bond in the resulting dipolar intermediate A
In this paper we present the synthesis, characterization and reactivity of interesting 1,2-oxazine N-oxides in which the heterocyclic ring is fused to the norbornane ring
The enamine substrate used as a 2π component in this study was 2-(4-morpholinyl)bicyclo [2.2.1]heptene (3)
Summary
The versatility of the conjugated nitroalkenes as synthetic tools in their reactions with nucleophilic olefins is known.[1,2,3,4,5,6,7,8,9] In the particular case in which the reacting centres are prochiral, the approach of the two reactants can be either like or unlike[8] and the first step involves the diastereoselective formation of a new carbon-carbon bond in the resulting dipolar intermediate A.
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