Asymmetric catalysis, synthesis and chirality
A selection of some recent advances in synthesis, catalysis and stereochemistry are listed. Highlights appeared among others in Science, Chem. Tech., Chem.& Ind., Nachrichten, Chem. World, Chem. Science, Angew. Chem. Int. Ed., JACS beta, Manufacturing Chemist, Nature, Chem. Eng. News.:
- First enantioselective conjugate addition of organometallic reagents (organozinc) with complete stereocontrol
- Chiral monodentate ligands, Phosphoramidites as privileged ligands induced a paradigm shift in chiral catalyst design
- Asymmetric hydrogenation resulting in implementation of industrial process for asymmetric hydrogenation leading to drug intermediate on multiton scale (at DSM company)
- First highly enantioselective and practical catalytic conjugate addition of Grignard reagents
- Mixed monodentate ligand approach in asymmetric catalysis
- DNA based asymmetric catalysis in water
- Color test for enantiomeric excess determination
- Discovery of asymmetric heteroallylic substitution
- New catalytic methods for stereoselective glycosidic bond formation
- Catalytic asymmetric total synthesis of e.g. prostaglandin, insect pheromones, mycobacterial tuberculosis antigen, phytophtora fungi hormone, natural butenolides, mycocerosic acid, antitumor phaseolinic acid, etc.
- Ligand accelerated copper-catalyzed click reaction
- Catalytic asymmetric synthesis of beta amino acids via anti-Markovnikov type Wacker oxidation
- First Mn-based catalytic asymmetric dihydroxylation
- Catalytic Asymmetric Friedel Crafts in water
- Astrophysically relevant mechanism for chiral amplification of amino acids
- Enantioconvergent Chemoenzymatic Synthesis of Optically Active alpha-Substituted Amides
- First catalytic enantioselective allylic alkylation with organolithium compounds
- Mild and efficient cross coupling with organolithium compounds
The use of monodentate chiral ligands (phosphoramidites) has resulted in a paradigm shift in asymmetric catalysis (it was demonstrated that bidentate chiral ligands are not a sine qua non to achieve high enantioselectivity in transition metal catalysis). The first highly enantioselective catalytic 1,4-addition with Grignard reagents and allylic alkylation with organolithium compounds, key synthetic transformations, solved longstanding issues in the field of asymmetric catalysis. Taming organolithium reagents for selective cross coupling has recently been reported from our laboratories. A major advance is also the design of the first DNA-based asymmetric catalysis in water including enantioselective addition of water in water.