Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity.
Org Biomol Chem
; 11(21): 3451-60, 2013 Jun 07.
Article
em En
| MEDLINE
| ID: mdl-23411590
ABSTRACT
A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,ß-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%) and high enantioselectivity (up to 99%). The experimental results and DFT calculations suggest that para substituted aromatic aldehydes as substrate show higher ee in the product than their ortho/meta counterparts. The (1)H and (13)C NMR spectra study corroborated the calculated results. The chiral organocatalyst can be easily synthesized from optically pure phenylalanine in two simple steps with 90% overall yield.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos de Tosil
/
Simulação por Computador
/
Aldeídos
/
Amidas
/
Aminoácidos
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article