Asymmetric synthesis of ß-hydroxy-α-amino phosphonic acid derivatives via organocatalytic direct aldol reaction of α-isothiocyanato phosphonates with aldehydes.
J Org Chem
; 78(20): 10541-7, 2013 Oct 18.
Article
en En
| MEDLINE
| ID: mdl-24053407
ABSTRACT
α-Isothiocyanato phosphonates are first used as nucleophiles to react with aldehydes for the asymmetric synthesis of ß-hydroxy-α-amino phosphonic acid derivatives. The process is catalyzed by a quinine-derived thiourea via cascade aldol/cyclization reaction, affording a wide range of protected ß-hydroxy-α-amino phosphonates containing adjacent quaternary-tertiary stereocenters in up to 93% yield, up to 81% ee, and >991 dr. This work represents the first example of α-isothiocyanato phosphonates serving as nucleophiles that are used in the catalytic asymmetric synthesis.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Ácidos Fosforosos
/
Tiourea
/
Isotiocianatos
/
Aldehídos
/
Aminoácidos
Idioma:
En
Revista:
J Org Chem
Año:
2013
Tipo del documento:
Article
País de afiliación:
China