A four-step approach for the synthesis of dihydroxylated piperidine, quinolizidine and indolizidine systems is
described employing α,β-unsaturated diazoketones as versatile building blocks. Unsaturated diazoketones were readily
prepared from a Horner-Wadsworth-Emmons reaction between a diazophosphonate and amino-aldehydes. The strategy
employs an asymmetric dihydroxylation reaction as the key step and is simple and straightforward enough to be extended
to other nitrogen heterocycles.
Keywords: Diazocompounds, glucosidases, indolizidines, piperidines, quinolizidines, α, β-unsaturated diazoketones.
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