a-Methylserinals as an access to a-methyl-ß-hydroxyamino acids: Application in the synthesis of all stereoisomers of a- methylthreonine

The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level o...

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Detalhes bibliográficos
Autores: Avenoza, A. [0000-0002-5465-3555], Busto, J.H. [0000-0003-4403-4790], Corzana, F. [0000-0001-5597-8127], Peregrina, J.M. [0000-0003-3778-7065], Sucunza, D. [0000-0002-3307-4204], Zurbano, M.M. [0000-0001-6370-3537]
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2004
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/5bbc690cb750603269e81425
Acesso em linha:https://investigacion.unirioja.es/documentos/5bbc690cb750603269e81425
Access Level:acceso abierto
Descrição
Resumo:The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different β-substituted α-methylserines. © 2003 Elsevier Ltd. All rights reserved.