Diastereoisomeric pyrazolone-fused spirocyclohexenimines, bearing contiguous all-carbon quaternary and tertiary stereocenters, are readily synthesized for the first time in good to excellent yield (up to 98%) and high enantioselectivity (up to 97% ee) via vinylogous Michael reaction/cyclization cascade reaction of a-arylidene pyrazolones and a,a-dicyanoalkylidenes. The formal [4+2] atom-economical annulation proceeds with commercially available Takemoto’s catalyst under mild reaction conditions.

Asymmetric Synthesis of Pyrazolone Fused Spirocyclohexeneimines via a Vinylogous Michael/Cyclization Cascade Reaction

Meninno, Sara
Methodology
;
Lattanzi, Alessandra
Writing – Review & Editing
2019-01-01

Abstract

Diastereoisomeric pyrazolone-fused spirocyclohexenimines, bearing contiguous all-carbon quaternary and tertiary stereocenters, are readily synthesized for the first time in good to excellent yield (up to 98%) and high enantioselectivity (up to 97% ee) via vinylogous Michael reaction/cyclization cascade reaction of a-arylidene pyrazolones and a,a-dicyanoalkylidenes. The formal [4+2] atom-economical annulation proceeds with commercially available Takemoto’s catalyst under mild reaction conditions.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4719860
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