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Título

Base-controlled diastereodivergent synthesis of (R)- and (S)-2-substituted-4-alkylidenepiperidines by the wadsworth−emmons reaction

AutorEtayo, Pablo; Badorrey, Ramón ; Díaz-de-Villegas, María D.; Gálvez, José A.
Fecha de publicaciónene-2007
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 72(3): 1005-1008 (2007)
ResumenSignificant base and reaction time effects have been observed in the Wadsworth−Emmons reaction between a chiral 2-substituted-4-oxopiperidine and phosphonates. In the reactions carried out using a large excess of DBU as the base and prolonged reaction times, the initially formed 2R products epimerized into thermodynamically more stable products through a retro-conjugate/conjugate addition sequence and 2-substituted-4-alkylidenepiperidines of 2S configuration were selectively synthesized. In contrast, when the reaction was carried out using LDA as the base, epimerization did not occur and 2-substituted-4-alkylidenepiperidines of 2R configuration were obtained with excellent yields.
Descripción4 pages, 3 schemes, 3 tables.-- Supporting Information Available: http://pubs.acs.org.
Versión del editorhttp://dx.doi.org/10.1021/jo062075c
URIhttp://hdl.handle.net/10261/19363
DOI10.1021/jo062075c
ISSN0022-3263
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