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Switch in regioselectivity of epoxide ring-opening by changing the organometallic reagent

AuthorsGálvez, José A. ; Díaz de Villegas, María D. ; Badorrey, Ramón ; López-Ram-de-Víu, Pilar
Issue Date2011
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 9(23): 8155-8162 (2011)
AbstractThe regio- and stereoselective ring-opening of a 2-(2′-oxiranyl)-1,2,3,6-tetrahydropyridine using organometallic reagents is reported. The choice of the organometallic reagent determines the formation of either 2-[(R)-1-hydroxyalkyl]- or 2-[(S)-2-hydroxy-1-alkyl]-1,2,3,6-tetrahydropyridines. The formation of 2-[(S)-2-hydroxy-1-alkyl]-1,2,3,6-tetrahydropyridines is a rare example of epoxide ring-opening with retention of configuration. The process has been applied to the asymmetric synthesis of β-(+)-conhydrine and to the formal synthesis of (2S,2′R)-erythro-methylphenidate from a common precursor. Extension of the structural diversity of the process has allowed the synthesis of several β-(+)-conhydrine analogs.
Identifiersdoi: 10.1039/C1OB06216F
issn: 1477-0520
e-issn: 1477-0539
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