Stereocontrol in the EtAlCl(2)-induced cyclization of chiral gamma,delta-unsaturated methyl ketones to form cyclopentanones.
J Org Chem
; 68(16): 6451-4, 2003 Aug 08.
Article
em En
| MEDLINE
| ID: mdl-12895088
ABSTRACT
EtAlCl(2)-induced cyclization of chiral gamma,delta-unsaturated ketones 11c and 17b takes place mainly from the expected face. The selectivity is modest for 11c (6040) in which the large substituent is a primary alkyl group and the medium substituent is a methyl group and excellent for 17b (937) in which the large substituent is a cyclohexyl group and the medium substituent is a methyl group. The cyclization of 17a is anomalous, suggesting that the phenyl group has more than a simple steric effect.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Organometálicos
/
Ciclopentanos
/
Cetonas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2003
Tipo de documento:
Article
País de afiliação:
Estados Unidos