Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous Nucleophilicity under Dinuclear Zinc Catalysis
- 12 March 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (13), 4572-4573
- https://doi.org/10.1021/ja809723u
Abstract
Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the γ-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.Keywords
This publication has 32 references indexed in Scilit:
- Exploiting Orthogonally Reactive Functionality: Synthesis and Stereochemical Assignment of (−)-Ushikulide AJournal of the American Chemical Society, 2008
- Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Acyclic 2‐Substituted‐1,3‐Propanediols: A Powerful Entry into Chiral Building BlocksChemistry – A European Journal, 2008
- Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc CatalystJournal of the American Chemical Society, 2008
- Asymmetric Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by C2-Symmetric Tridentate Bis(oxazoline) and Bis(thiazoline) Zinc ComplexesJournal of the American Chemical Society, 2006
- Copolymerization of Cyclohexene Oxide with CO2 by Using Intramolecular Dinuclear Zinc CatalystsChemistry – A European Journal, 2005
- Catalytic Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Well-Defined Chiral Ru Amido ComplexesJournal of the American Chemical Society, 2004
- Highly Enantioselective Cr(salen)-catalyzed Reaction of 2-(Trimethylsilyloxy)furan and Aldehydes. Effect of Alcohol on EnantioselectivityChemistry Letters, 2003
- Dinuclear zinc(II) complex of a new acyclic phenol-based dinucleating ligand with four methoxyethyl chelating arms: first dizinc model with aminopeptidase functionJ. Chem. Soc., Dalton Trans., 1999
- Syntheses and characterization of novel tri- and hexa-nuclear zinc complexes with biomimetic chelate ligandsJ. Chem. Soc., Dalton Trans., 1996
- Furan-, Pyrrole-, and Thiophene-Based Siloxydienes for Syntheses of Densely Functionalized Homochiral CompoundsSynthesis, 1995