Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
Org Lett
; 8(20): 4633-6, 2006 Sep 28.
Article
em En
| MEDLINE
| ID: mdl-16986968
ABSTRACT
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Flúor
/
Aminoácidos
Idioma:
En
Ano de publicação:
2006
Tipo de documento:
Article