Organocatalytic asymmetric addition of alcohols and thiols to activated electrophiles: efficient dynamic kinetic resolution and desymmetrization protocols.
J Org Chem
; 73(16): 6409-12, 2008 Aug 15.
Article
em En
| MEDLINE
| ID: mdl-18646859
ABSTRACT
Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine-, methionine-, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantioselectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Compostos de Sulfidrila
/
Alcaloides de Cinchona
/
Álcoois
/
Aminoácidos
/
Lactonas
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article