Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions.
J Org Chem
; 81(6): 2494-505, 2016 Mar 18.
Article
em En
| MEDLINE
| ID: mdl-26914694
ABSTRACT
The effects of substituents and cavity size on catalytic efficiency of proline-rich cyclopeptoids under phase-transfer conditions were studied. High affinity constants (Ka) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylglycine/L-proline hexameric cyclopeptoid. This compound was found to catalyze the alkylation of N-(diphenylmethylene)glycine cumyl ester in values of enantioselectivities comparable with those reported for the Cinchona alkaloid ammonium salts derivatives (83-96% ee), and with lower catalyst loading (1-2.5% mol), in the presence of a broad range of benzyl, allyl and alkyl halides.
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Peptídeos Cíclicos
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Arginina
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Derivados de Benzeno
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Prolina
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Alcaloides de Cinchona
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Glicina
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2016
Tipo de documento:
Article
País de afiliação:
Itália