Asymmetric Synthesis of (+)-(S,S)-Reboxetine via a New (S)-2-(Hydroxymethyl)morpholine Preparation

Asymmetric Synthesis of (+)-(S,S)-Reboxetine via a New (S)-2-(Hydroxymethyl)morpholine Preparation

(S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps. Key steps were selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution.

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Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2005-03, Vol.7 (5), p.937-939
Hauptverfasser: Brenner, Eric, Baldwin, Ronald M, Tamagnan, Gilles
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Indicators and Reagents
Molecular Structure
Morpholines - analysis
Morpholines - chemical synthesis
Morpholines - chemistry
Oxidation-Reduction
Stereoisomerism
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Beschreibung
Zusammenfassung:(S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps. Key steps were selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050059g