5-(pyrrolidin-2-yl)-1H-tetrazole and 5-[(pyrrolidin-2-yl)methyl]-1H-tetrazole: proline surrogates with increased potential in asymmetric catalysis.
Catalytic enantioselective methodology has dramatically been enriched by the re-discovery of the simple amino acid proline as a chiral catalyst in the year 2000. Although no catalyst offers such a simple and broad access to quite complex reaction products, as does proline, its synthetic potential is not unrestricted, what is especially connected to its poor solubility in organic media. Exchange of the carboxylic moiety by a tetrazole unit leads to proline surrogates, that by far outperform proline with respect to yield, enantioselectivity, reaction time, substrate and solvent scope, catalyst loading, and stoichiometry of the compounds used in excess. These factors are discussed and critically compared with selected representative proline-catalyzed reactions.
Limbach
Michael
M
Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland. michael.limbach@org.chem.ethz.ch
D002384:Catalysis; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D011758:Pyrroles / Q000737:chemistry* / Q000378:metabolism; D011759:Pyrrolidines / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry* / Q000378:metabolism
D011758:Pyrroles; D011759:Pyrrolidines; D013777:Tetrazoles; C045574:1H-tetrazole; D011392:Proline