α,β-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines

Title:α,β-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines

Volume: 13 Issue: 17

Author(s): Barbara Bernardim, Leonardo D. Lordello and Antonio C.B. Burtoloso

Affiliation:

Keywords: Diazocompounds, glucosidases, indolizidines, piperidines, quinolizidines, α, β-unsaturated diazoketones.

Abstract: 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.

Cite this article as:

Bernardim Barbara, Lordello D. Leonardo and Burtoloso C.B. Antonio, α,β-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines, Current Topics in Medicinal Chemistry 2013; 13 (17) . https://dx.doi.org/10.2174/15680266113139990145