A one-pot C-H insertion/olefination sequence for the formation of α-alkylidene-γ-butyrolactones.
Org Lett
; 16(10): 2772-5, 2014 May 16.
Article
em En
| MEDLINE
| ID: mdl-24788001
ABSTRACT
A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene-γ-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.
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Base de dados:
MEDLINE
Assunto principal:
4-Butirolactona
/
Alcenos
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article