Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks.
J Org Chem
; 74(15): 5652-5, 2009 Aug 07.
Article
em En
| MEDLINE
| ID: mdl-19518106
ABSTRACT
This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with omega-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Piperazinas
/
Azepinas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2009
Tipo de documento:
Article
País de afiliação:
Dinamarca