A novel organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of alpha-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.

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

MARINI, Francesca
;
STERNATIVO, Silvia;DEL VERME, FRANCESCA;TESTAFERRI, Lorenzo;TIECCO, Marcello
2009

Abstract

A novel organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of alpha-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.
2009
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/152106
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