Titanium(IV) chloride-mediated carbon-carbon bond-forming reaction between 3,3-dialkylcyclobutanones and aldehydes.
Org Lett
; 12(17): 3960-2, 2010 Sep 03.
Article
em En
| MEDLINE
| ID: mdl-20690661
ABSTRACT
Treatment of 3,3-dialkylcyclobutanones with titanium(IV) chloride in the presence of aldehyde gave beta'-chloro-beta-hydroxy ketones in high yields. It was speculated that ring cleavage of the cyclobutanone ring with titanium(IV) chloride gave trichlorotitanium enolate having a tertiary alkyl chloride moiety and then aldol reaction of the titanium enolate proceeded. A trialkylsilylmethyl group at the 2-position of cyclobutanone facilitated the ring cleavage. Synthesis of substituted cyclopentenone from an obtained product is also described.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Titânio
/
Compostos de Organossilício
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Ciclobutanos
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Ciclopentanos
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Aldeídos
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Hidrocarbonetos Clorados
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Cetonas
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2010
Tipo de documento:
Article