Asymmetric Michael Addition of 5 H-Oxazol-4-ones to Vinyl Sulfones: Stereoselective Synthesis of Monofluorinated Analogs of 2-Tertiary Hydroxyl-3-Methyl-Substituted Carboxylic Acidl Derivatives

An asymmetric Michael addition of 5H‐oxazol‐4‐ones to vinyl sulfones has been developed. In the presence of 10 mol % of quinine‐based benzyl‐substituted thiourea as catalyst at 0 °C, the products could be obtained with excellent enantio‐ and diastereoselectivity (up to>99 % ee and>20:1 dr). 1....

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2014-12, Vol.356 (18), p.3777-3783
Main Authors: Liu, Qian, Qiao, Baokun, Chin, Kek Foo, Tan, Choon-Hong, Jiang, Zhiyong
Format: Article
Language:English
Subjects:
2-tertiary hydroxyl-3-methyl-substituted carboxylic acids
5 H-oxazol-4-ones
Asymmetric organocatalysis
Monofluorination
Vinyl sulfones
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Summary:An asymmetric Michael addition of 5H‐oxazol‐4‐ones to vinyl sulfones has been developed. In the presence of 10 mol % of quinine‐based benzyl‐substituted thiourea as catalyst at 0 °C, the products could be obtained with excellent enantio‐ and diastereoselectivity (up to>99 % ee and>20:1 dr). 1.0 mol % of catalyst also produced the corresponding adducts with similar stereoselective results when the temperature was increased to 25 °C. The obtained adducts have been demonstrated as significant synthetic fragments to conveniently access the monofluorinated analogs of biologically important 2‐tertiary hydroxyl‐3‐methyl‐substituted carboxylic acid derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400649