Dual Lewis acid-Lewis base activation in enantioselective cyanation of aldehydes using acetyl cyanide and cyanoformate as cyanide sources.
J Am Chem Soc
; 127(33): 11592-3, 2005 Aug 24.
Article
em En
| MEDLINE
| ID: mdl-16104722
ABSTRACT
Dual activation by a chiral Lewis acid and an achiral or chiral Lewis base enabled cyanation of both aromatic and aliphatic aldehydes with acetyl cyanide and ethyl cyanoformate to provide direct access to O-acetylated and O-alkoxycarbonylated cyanohydrins, respectively, under mild conditions. With a combination of a Ti-salen catalyst and Et3N, benzaldehyde was converted to the O-acetylated cyanohydrin with 94% ee within 10 h at -40 degrees C in 89% isolated yield.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Cianetos
/
Aldeídos
/
Nitrilas
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2005
Tipo de documento:
Article