A Highly Enantioselective Conjugate Reduction of 3-Arylinden-1-ones Using Bakers' Yeast for the Preparation of (S)-3-Arylindan-1-ones

The bakers' yeast reduction of 3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-one 4 has been shown to give (S)-3-(1,3-benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-indan-1-one 6 in 65% yield with high enantioselectivity (>99.0% ee), a key intermediate for the synthesis of the endothelin receptor...

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Bibliographic Details
Published in:Organic letters 1999-12, Vol.1 (11), p.1839-1842
Main Authors: Clark, William M, Kassick, Andrew J, Plotkin, Michael A, Eldridge, Ann M, Lantos, Ivan
Format: Article
Language:English
Subjects:
Carboxylic Acids - chemical synthesis
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Endothelin Receptor Antagonists
Hydrogen-Ion Concentration
Indans - chemical synthesis
NADP
Oxidation-Reduction
Saccharomyces cerevisiae
Stereoisomerism
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Summary:The bakers' yeast reduction of 3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-one 4 has been shown to give (S)-3-(1,3-benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-indan-1-one 6 in 65% yield with high enantioselectivity (>99.0% ee), a key intermediate for the synthesis of the endothelin receptor antagonist SB 217242. In addition, the substituted 3-arylinden-1-ones 10a − e gave equally high enantioselectivity for the 3-arylindan-1-one products 13a − e. Mechanistic studies of the reaction indicate the operative pathway to be an asymmetric conjugate reduction, wherein the hydride transfer from NAD(P)H occurs from the Re-face of the indenone substrate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol991111+