Stereocontrolled synthesis of 1,2- and 1,3-diamine building blocks from aziridine aldehyde dimers.
J Org Chem
; 78(23): 11637-45, 2013 Dec 06.
Article
em En
| MEDLINE
| ID: mdl-23957736
ABSTRACT
Vicinal aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich reaction. Subsequent solvent- and/or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamines with high regioselectivity. The ring opening is also influenced by the substitution at the C3 position of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
Canadá