Solvent-controlled diastereoselectivity in tryptophan-catalyzed Mannich reactions
Solvent effects in the L-tryptophan-catalyzed Mannich reaction between hydroxyacetone and glyoxylate imines have been examined. The use of a DMSO/1-butanol (4:1 v/v) mixture as solvent at rt provided the expected Mannich adducts in good yields, high anti-diastereoselectivity (up to 10.3:1 anti/syn r...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2015 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/119967 |
| Acceso en línea: | https://hdl.handle.net/2445/119967 |
| Access Level: | acceso abierto |
| Palabra clave: | Aminoàcids Catàlisi asimètrica Amino acids Enantioselective catalysis |
| Sumario: | Solvent effects in the L-tryptophan-catalyzed Mannich reaction between hydroxyacetone and glyoxylate imines have been examined. The use of a DMSO/1-butanol (4:1 v/v) mixture as solvent at rt provided the expected Mannich adducts in good yields, high anti-diastereoselectivity (up to 10.3:1 anti/syn ratio) and excellent enantioselectivities (up to >99.9% ee for the anti isomer) |
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