α-Allyl-α-aryl α-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.
J Org Chem
; 79(11): 5359-64, 2014 Jun 06.
Article
en En
| MEDLINE
| ID: mdl-24828423
ABSTRACT
Allylating agents were explored for the asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem N-alkylation/π-allylation. Cross-metathesis of the tandem product was developed to provide allylic diversity not afforded in the parent reaction; the synthesis of homotyrosine and homoglutamate analogues was completed. Cyclic α-amino acid derivatives could be accessed by ring-closing metathesis presenting a viable strategy to higher ring homologue of enantioenriched α-substituted proline. The eight-membered proline analogue was successfully converted to the pyrrolizidine natural product backbone.
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1
Banco de datos:
MEDLINE
Asunto principal:
Alcaloides de Pirrolicidina
/
Prolina
/
Aminoácidos Cíclicos
Idioma:
En
Año:
2014
Tipo del documento:
Article