The asymmetric vinylogous Mannich reaction of dicyanoalkylidenes with α-amido sulfones under phase-transfer conditions
- 26 March 2007
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 16,p. 1620-1622
- https://doi.org/10.1039/b702172k
Abstract
The stereoselective vinylogous Mannich reaction of dicyanoalkylidenes under phase-transfer catalytic conditions utilizing stable α-amido sulfones as imine precursors is presented; a rigid pyrrolidinium salt acts as the phase-transfer catalyst, giving access to the amino alkylated products in generally good yield and up to 95% ee.Keywords
This publication has 35 references indexed in Scilit:
- Phase‐Transfer‐Catalyzed Enantioselective Mannich Reaction of Malonates with α‐Amido SulfonesAdvanced Synthesis & Catalysis, 2006
- Organocatalytic Asymmetric Deconjugative Michael AdditionsThe Journal of Organic Chemistry, 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
- 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
- Organocatalytic asymmetric allylic carbon–carbon bond formationOrganic & Biomolecular Chemistry, 2005
- Enantioselective Organocatalytic Allylic AminationJournal of the American Chemical Society, 2005
- Exploring Phase-Transfer Catalysis with Molecular Dynamics and 3D/4D Quantitative Structure−Selectivity RelationshipsJournal of Chemical Information and Modeling, 2005
- Direct Organocatalytic and Highly Enantio‐ and Diastereoselective Mannich Reactions of α‐Substituted α‐CyanoacetatesAngewandte Chemie International Edition in English, 2005
- Transition Metal Salt-Catalyzed Direct Three-Component Mannich Reactions of Aldehydes, Ketones, and Carbamates: Efficient Synthesis of N-Protected β-Aryl-β-Amino Ketone CompoundsThe Journal of Organic Chemistry, 2004
- Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid DerivativesJournal of the American Chemical Society, 2001