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Issue 23, 2011
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Switch in regioselectivity of epoxide ring-opening by changing the organometallic reagent

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Abstract

The 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.

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

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Publication details

The article was received on 20 Jul 2011, accepted on 02 Sep 2011 and first published on 05 Sep 2011


Article type: Paper
DOI: 10.1039/C1OB06216F
Org. Biomol. Chem., 2011,9, 8155-8162

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

    J. A. Gálvez, M. D. Díaz de Villegas, R. Badorrey and P. López-Ram-de-Víu, Org. Biomol. Chem., 2011, 9, 8155
    DOI: 10.1039/C1OB06216F

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