A New Stereoselective Synthesis of Cyclopropanes Containing Quaternary Stereocentres via Organocatalytic Michael Addition to Vinyl Selenones

Autor: Francesca Marini, Lorenzo Testaferri, Silvia Sternativo, Marcello Tiecco, Francesca Del Verme
Jazyk: angličtina
Rok vydání: 2009
Předmět:
Popis: A novel organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of α-substituted cyanoacetates to easily accessible vinyl selenones catalyzed by a bifunctional ureidic catalyst, smoothly cyclize by intramolecular alkylation induced by a de-ethoxycarbonylation process. The one-pot sequence generates cyclopropanes bearing adjacent tertiary and quaternary stereocentres as single Z-isomers in moderate to high yields and good enantiomeric excesses.
Databáze: OpenAIRE