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Type: Artigo de periódico
Title: Asymmetric reduction of prochiral ketones using 6 in situ generated oxazaborolidine derived from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol. An efficient synthesis of enantiopure (R)-tomoxetine
Author: Lapis, AAM
de Fatima, A
Martins, JED
Costa, VEU
Pilli, RA
Abstract: Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst 2 prepared in situ from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorborman-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (7-5-94%), except for ketones bearing eletron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine. a potent anti-depressant drug. (C) 2004 Elsevier Ltd. All rights reserved.
Subject: oxazaborolidine
asymmetric reduction
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 46, n. 3, n. 495, n. 498, 2005.
Rights: fechado
Identifier DOI: 10.1016/j.tetlet.2004.11.052
Date Issue: 2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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