| Title | Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and a-hydroxy-ß-amino esters |
|---|---|
| Authors | CARMONA CARMONA, JOSÉ ALBERTO, de Gonzalo, Gonzalo , Serrano, Inmaculada , Crespo-Pena, Ana M. , Simek, Michal , Monge, David , Fernandez, Rosario , Lassaletta, Jose M. |
| External publication | Si |
| Means | Org. Biomol. Chem. |
| Scope | Article |
| Nature | Científica |
| JCR Quartile | 2 |
| SJR Quartile | 1 |
| JCR Impact | 3.423 |
| SJR Impact | 1.281 |
| Publication date | 14/04/2017 |
| ISI | 000399201600017 |
| DOI | 10.1039/c7ob00308k |
| Abstract | A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic alpha-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucosamine derived 3,5-bis-(trifluoromethyl) phenyl thiourea the reaction could be accomplished with high yields (75-98%) and moderate enantioselectivities (50-64% ee). Subsequent high-yielding and racemization-free tranformations of both aromatic-and aliphatic-substituted diazene products in a one pot fashion provide a direct entry to valuable azoxy compounds and alpha-hydroxy-beta-amino esters. |
| Universidad Loyola members |