| Summary: | A stereoselective approach has been developed for the flexible synthesis of substituted 2-pyrrolidones and 2-piperidones. By employing the key Overman rearrangement, efficient transfer of stereochemistry was achieved, and an acylation and ring closing metathesis strategy afforded a library of target N-heterocycles. In addition, the optimisation of a synthesis of 4-oxopipecolic acid derivatives from L-aspartic acid was investigated. A novel, milder and higher yielding 6-endo-trig cyclisation procedure was developed. This allowed for the generation of a library of 2,6-cis-substituted 4-oxopipecolic derivatives. Stereoselective carbonyl reduction extended the synthesis further to include 4-hydroxypipecolic acid derivatives.
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