Enantioselective organocatalytic Michael addition of aldehydes to beta-nitrostyrenes
Marju Laars1, Kerti Ausmees, Merle Uudsemaa
1Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.
Abstract:
The utility of C(2)-symmetric bipiperidine and bimorpholine derivatives as organocatalysts in the Michael addition of enamine intermediates formed from aldehydes to nitroolefins has been demonstrated. The best results were obtained when the reaction was run in the presence of (2R,2'R)-N-iPr-bipiperidine. The products were formed via an enamine intermediate with high diastereo- and enantioselectivity with relatively short reaction times.
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Radical Anti-Markovnikov Addition to Alkenes: Overview
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Base-Catalyzed Aldol Addition Reaction


