Organocatalytic and Highly Stereoselective Direct Vinylogous Mannich Reaction
- 31 January 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (7) , 1878-1879
- https://doi.org/10.1021/ja068703p
Abstract
The first direct asymmetric vinylogous Mannich (AVM) reaction of α,α-dicyanoolefins and N-Boc aldimines was described promoted by a simple chiral bifunctional thiourea-tertairy amine organocatalyst. The reaction was highly efficient (S/C up to 1000) and regio-, stereoselective (generally >99% de, 96 to >99.5% ee) at room temperature for a broad array of substrates. Enantiomerically pure δ-amino acid could be smoothly prepared from the adduct.Keywords
This publication has 18 references indexed in Scilit:
- A Highly Efficient and Practical Method for Catalytic Asymmetric Vinylogous Mannich (AVM) ReactionsAngewandte Chemie International Edition in English, 2006
- The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino AcidsJournal of the American Chemical Society, 2006
- Organocatalytic and direct asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydesChemical Communications, 2006
- Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivativeChemical Communications, 2006
- Bifunctional‐Thiourea‐Catalyzed Diastereo‐ and Enantioselective Aza‐Henry ReactionChemistry – A European Journal, 2005
- Enantioselective Thiourea‐Catalyzed Acyl‐Mannich Reactions of IsoquinolinesAngewandte Chemie International Edition in English, 2005
- Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of FuranJournal of the American Chemical Society, 2004
- Activation of Carbonyl Compounds by Double Hydrogen Bonding: An Emerging Tool in Asymmetric CatalysisAngewandte Chemie International Edition in English, 2004
- Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic AcidsJournal of the American Chemical Society, 2004
- Vinylogous Mannich Reactions. The Asymmetric Total Synthesis of (+)-CroomineJournal of the American Chemical Society, 1996