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Title: | Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof |
Authors: | Fernández, Rosario; Ros, Abel CSIC ORCID CVN ; Magriz, Antonio CSIC; Dietrich, Hansjörg; Lassaletta, José M. CSIC ORCID | Keywords: | Asymmetric catalysis Amines Transfer hydrogenation Dynamic kinetic resolution |
Issue Date: | 7-May-2007 | Publisher: | Elsevier | Citation: | Tetrahedron 63(29): 6755-6763 (2007) | Abstract: | The diastereo- and enantioselective syntheses of trans-cycloalkyl amines was accomplished through a three-step sequence consisting of: (1) asymmetric transfer hydrogenation through dynamic kinetic resolution of bicyclic and monocyclic α-substituted ketones using HCO2H/Et3N as the hydrogen source and TsDPEN-based Ru(II) catalysts, (2) nucleophilic hydroxyl to azide substitution of the resulting cis-cycloalkanols using diphenyl phosphoryl azide under modified Mitsunobu conditions, and (3) reduction of the trans-azide intermediates with LiAlH4 of PPh3/H2O to the desired targets. | Description: | 9 páginas, 1 figura, 2 tablas, 6 esquemas. | Publisher version (URL): | http://dx.doi.org/10.1016/j.tet.2007.04.075 | URI: | http://hdl.handle.net/10261/37870 | DOI: | 10.1016/j.tet.2007.04.075 | ISSN: | 0040-4020 |
Appears in Collections: | (IIQ) Artículos |
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