Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines.
J Org Chem
; 68(16): 6264-7, 2003 Aug 08.
Article
em En
| MEDLINE
| ID: mdl-12895059
ABSTRACT
The reaction of chiral sulfinimines 1c-g derived from aliphatic aldehydes with TMSCN in the presence of CsF gave alpha-amino nitriles in high diastereoselectivity and yield. alpha,beta-Diamino acid derivatives were also obtained in high diastereoselectivity from the reaction of 2-aziridinesulfinimines 1h and 1i followed by ring-opening of the products with thiophenol. The presence of hydrogen at the alpha-position of the C=N double bond is crucial in this TMSCN addition reaction.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article