Synthesis of enantiopure (aMe)Dip and other a-methylated ß-branched amino acid derivatives

This report describes the synthesis of the two enantiomerically pure α-methylated β-branched phenylalanine derivatives, (S)- and (R)-α-methyl-β,β-diphenylalanine - (αMe)Dip - starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-α-methylserine methyl esters, respectively. Th...

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Detalles Bibliográficos
Autores: Avenoza, A. [0000-0002-5465-3555], Busto, J.H. [0000-0003-4403-4790], Cativiela, C., Peregrina, J.M. [0000-0003-3778-7065], Sucunza, D. [0000-0002-3307-4204], Zurbano, M.M. [0000-0001-6370-3537]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2003
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/5bbc690ab750603269e813f5
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc690ab750603269e813f5
Access Level:acceso abierto
Descripción
Sumario:This report describes the synthesis of the two enantiomerically pure α-methylated β-branched phenylalanine derivatives, (S)- and (R)-α-methyl-β,β-diphenylalanine - (αMe)Dip - starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-α-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other α-methylated β-branched serine derivatives is also described. © 2003 Elsevier Science Ltd. All rights reserved.

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