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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|
De Fatima 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.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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