Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael an...

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Detalles Bibliográficos
Autores: Pérez-Fernández, M. [0000-0002-4620-6333], Avenoza, A. [0000-0002-5465-3555], Busto, J.H. [0000-0003-4403-4790], Peregrina, J.M. [0000-0003-3778-7065], Rodríguez, F.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2010
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc69a6b750603269e81f0d
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc69a6b750603269e81f0d
Access Level:acceso abierto
Palabra clave:5-hydroxyproline
Cyclobutane derivatives
Michael addition
Wittig reaction
Descripción
Sumario:The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.