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An expeditious method for the first asymmetric synthesis of dexoxadrol from the chiral pool

AuthorsEtayo, Pablo; Badorrey, Ramón ; Díaz-de-Villegas, María D.; Gálvez, José A. ; López-Ram-de-Víu, Pilar
Issue Date2010
CitationSynlett 12: 1775-1778 (2010)
AbstractA new, straightforward and high-yielding methodology for the asymmetric synthesis of 2-(1,3-dioxolan-4-yl)piperidines is described. This approach involves a highly stereoselective addition of vinylmagnesium bromide to N-(3-butenyl)imines derived from d-glyceraldehyde diphenyl ketal and a ring-closing metathesis reaction as key steps. This procedure was used for the first asymmetric synthesis of (S)-2-[(S)-2,2-diphenyl-1,3-dioxolan-4-yl]piperidine (dexoxadrol) starting from conveniently protected d-mannitol in six steps in 43% overall yield.
Identifiersdoi: 10.1055/s-0030-1258110
issn: 0936-5214
e-issn: 1437-2096
Appears in Collections:(ICMA) Artículos
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