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Closed Access item Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof

Authors:Fernández, Rosario
Ros, Abel
Magriz, Antonio
Dietrich, Hansjörg
Lassaletta, José M.
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
ISSN:0040-4020
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Appears in Collections:(IIQ) Artículos

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