Synthesis of cyclobutane serine analogues

(Chemical Equation Presented). In this paper, we describe a thermal [2 + 2] cycloaddition involving 2-acylaminoacrylates as electron-poor acceptor alkenes, a reaction that involves a Michael-Dieckmann-type process. The reaction gives rise to a new substituted cyclobutane skeleton that can be transfo...

ver descrição completa

Detalhes bibliográficos
Autores: Avenoza, A. [0000-0002-5465-3555], Busto, J.H. [0000-0003-4403-4790], Canal, N., Peregrina, J.M. [0000-0003-3778-7065]
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:España
Recursos:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc690db750603269e8143a
Acesso em linha:https://investigacion.unirioja.es/documentos/5bbc690db750603269e8143a
Access Level:acceso abierto
Descrição
Resumo:(Chemical Equation Presented). In this paper, we describe a thermal [2 + 2] cycloaddition involving 2-acylaminoacrylates as electron-poor acceptor alkenes, a reaction that involves a Michael-Dieckmann-type process. The reaction gives rise to a new substituted cyclobutane skeleton that can be transformed into amino acid derivatives. For example, a number of transformations were carried out to give the two pairs of stereoisomers of the 2-hydroxycyclobutane-α- amino acid serine analogue (c4Ser); compounds 22 and 23. This synthesis covers a gap in knowledge in the broad field of restricted amino acids.