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Type: Artigo de periódico
Title: Asymmetric Reduction Of Prochiral Ketones Using 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 A.A.M.
De Fatima A.
Martins J.E.D.
Costa V.E.U.
Pilli R.A.
Abstract: In this work, we report our results on the asymmetric reduction of prochiral aromatic and aliphatic ketones 3, 5-8 catalyzed by the novel in situ generated oxazaborolidine 2 derived from (1S,2S,3R,4R)-3-amino-7,7- dimethoxybornan-2-ol (1) and BH 3•Me 2S. This methodology was applied to the synthesis of the anti-depressant drug (R)-tomoxetine in three steps and 47% overall yield from 3-chloropropiophenone (3h). 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-dimethoxynorbornan-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (75-94%), except for ketones bearing electron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine, a potent anti-depressant drug. © 2004 Elsevier Ltd. All rights reserved.
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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