3335-74-8Relevant academic research and scientific papers
Organocatalytic conjugate addition of nitroalkanes to 3-ylidene oxindoles: A stereocontrolled diversity oriented route to oxindole derivatives
Quintavalla, Arianna,Lanza, Francesco,Montroni, Elisa,Lombardo, Marco,Trombini, Claudio
, p. 12049 - 12064 (2013)
An efficient and highly enantioselective Michael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifunctional organocatalysts. The stereochemistry at Cα and C β centers is perfectly controlled, and the intermediate C-3 enolate is trapped with a second Michael acceptor. The developed one-pot three-component consecutive reactions generate up to four contiguous stereocenters, including the C-3 all-carbon quaternary center, in a perfectly defined configuration. The conversion of the β-nitro oxindole into the corresponding β-amino derivative discloses synthetically useful transformations, exploitable to generate pharmaceutically attractive molecular targets.
