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Título

Efficient stereoselective synthesis of enantiopure cis- and trans-1,2,4-trisubstituted piperidines.

AutorEtayo, Pablo; Badorrey, Ramón ; Díaz-de-Villegas, María D.; Gálvez, José A.
Fecha de publicación26-nov-2007
EditorElsevier
CitaciónTetrahedron: Asymmetry 18(23): 2812-2819 (2007)
ResumenEnantiomerically pure (2R,4S)- and (2R,4R)-2-[(S)-1,2-dibenzyloxyethyl]-4-[2-(diphenylmethoxy)ethyl]-1-[(S)-1-phenylethyl]piperidines cis-1 and trans-1 have been synthesised from N-[(S)-1-phenylethyl]-(S)-2,3-di-O-benzylglyceraldimine in six steps in 31% and 18% overall yields, respectively. The efficiency of the synthetic strategy developed for the synthesis of these compounds relies on: (a) the totally diastereoselective tandem Mannich–Michael reaction between Danishefsky’s diene and the starting glyceraldimine, (b) the high yielding Wadsworth–Emmons reaction of the 4-piperidone intermediate and (c) the diastereodivergent reduction of the exocyclic C–C double bond at C4 of the piperidine ring. These transformations led to 1,2,4-trisubstituted piperidines with two new stereogenic centres with excellent stereoselectivity.
Descripción3 figures.
Versión del editorhttp://dx.doi.org/10.1016/j.tetasy.2007.10.042
URIhttp://hdl.handle.net/10261/19132
DOI10.1016/j.tetasy.2007.10.042
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