An efficient and highly enantioselective Michael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifunctional organocatalysts. The stereochemistry at C-alpha and C-beta 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 beta-nitro oxindole into the corresponding beta-amino derivative discloses synthetically useful transformations, exploitable to generate pharmaceutically attractive molecular targets.

Arianna Quintavalla, Francesco Lanza, Elisa Montroni, Marco Lombardo, Claudio Trombini (2013). Organocatalytic Conjugate Addition of Nitroalkanes to 3-Ylidene Oxindoles: A Stereocontrolled Diversity Oriented Route to Oxindole Derivatives. JOURNAL OF ORGANIC CHEMISTRY, 78, 12049-12064 [10.1021/jo402099p].

Organocatalytic Conjugate Addition of Nitroalkanes to 3-Ylidene Oxindoles: A Stereocontrolled Diversity Oriented Route to Oxindole Derivatives

QUINTAVALLA, ARIANNA;MONTRONI, ELISA;LOMBARDO, MARCO;TROMBINI, CLAUDIO
2013

Abstract

An efficient and highly enantioselective Michael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifunctional organocatalysts. The stereochemistry at C-alpha and C-beta 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 beta-nitro oxindole into the corresponding beta-amino derivative discloses synthetically useful transformations, exploitable to generate pharmaceutically attractive molecular targets.
2013
Arianna Quintavalla, Francesco Lanza, Elisa Montroni, Marco Lombardo, Claudio Trombini (2013). Organocatalytic Conjugate Addition of Nitroalkanes to 3-Ylidene Oxindoles: A Stereocontrolled Diversity Oriented Route to Oxindole Derivatives. JOURNAL OF ORGANIC CHEMISTRY, 78, 12049-12064 [10.1021/jo402099p].
Arianna Quintavalla;Francesco Lanza;Elisa Montroni;Marco Lombardo;Claudio Trombini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/260482
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