2024-03-28T14:03:43Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/651372016-08-17T08:49:37Zcom_10261_52707com_10261_5col_10261_52708
Switch in regioselectivity of epoxide ring-opening by changing the organometallic reagent
Gálvez, José A.
Díaz de Villegas, María D.
Badorrey, Ramón
López-Ram-de-Víu, Pilar
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.
Financial support from the Spanish Ministry of Science and Innovation and European Regional Development Fund (CTQ2008- 00187/BQU) and the Government of Aragón (GA E-71) is acknowledged.
Peer Reviewed
2013-01-25T12:34:44Z
2013-01-25T12:34:44Z
2011
2013-01-25T12:34:44Z
artículo
http://purl.org/coar/resource_type/c_6501
doi: 10.1039/C1OB06216F
issn: 1477-0520
e-issn: 1477-0539
Organic and Biomolecular Chemistry 9(23): 8155-8162 (2011)
http://hdl.handle.net/10261/65137
10.1039/C1OB06216F
en
none
Royal Society of Chemistry (UK)