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

AuthorsFernández, Rosario; Ros, Abel ; Magriz, Antonio ; Dietrich, Hansjörg; Lassaletta, José M.
KeywordsAsymmetric catalysis
Transfer hydrogenation
Dynamic kinetic resolution
Issue Date7-May-2007
CitationTetrahedron 63(29): 6755-6763 (2007)
AbstractThe 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.
Description9 páginas, 1 figura, 2 tablas, 6 esquemas.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2007.04.075
Appears in Collections:(IIQ) Artículos
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