Abstract
Nitrones 5 were prepared starting from N-benzylalaninol 3. Michael addition of 3 to 3-butenone-2 afforded alcohol 4 which was converted to 5 by Swern oxidation and subsequent treatment of the resulting aldehyde with N-alkylhydroxylamines. The enolate group of nitrones 6 generated by treatment of 5 with LDA acted as dipolarophile attacking the nitrone group to give the bicyclic compounds 7 by a spontaneous intramolecular cycloaddition. This took place with high diastereoselectivity affording only one diastereomer in 23 to 65% yield. The two substituents at position 4 give rise to a change in conformation of compounds 7 compared to compounds 8 unsubstituted at this position.
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