title: Α,β-unsaturated diazoketones as versatile building blocks for the synthesis of hydroxylated piperidines, indolizidines and quinolizidines.
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.
authors: Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil. antonio@iqsc.usp.br.
authors: Barbara
authors: B
authors: Bernardim
authors: Leonardo D
authors: LD
authors: Lordello
authors: Antonio C B
authors: AC
authors: Burtoloso
mesh_terms: D003979:Diazonium Compounds / Q000737:chemistry*; D054836:Indolizidines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D054837:Quinolizidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003979:Diazonium Compounds; D054836:Indolizidines; D010880:Piperidines; D054837:Quinolizidines; C032727:piperidine