A Convenient Synthesis of 3-Fluorinated 2-Oxopropyl Sulphoxides from Fluorinated Lithium Acetates and 1-Lithioalkyl Sulphoxides
- 1 January 1986
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1986 (07) , 579-582
- https://doi.org/10.1055/s-1986-31714
Abstract
Optically pure methyl 4-methylphenyl sulphoxide and ethyl 4-methylphenyl sulphoxide are metallated with lithium diisopropylamide and then subjected to the reaction with fluorinated lithium acetates or acetic esters. C-Acylation proceeds smoothly and regioselectively to give high yields of chiral 3-fluorinated 2-oxopropyl 4-methylphenyl sulphoxides. The analogous reaction of dimethyl sulphoxide with fluorinated lithium acetates affords good yields of racemic 3-fluorinated 2-oxopropyl methyl sulphoxides. As examples of further reactions of the products, C-methylation, S-deoxygenation, and carbonyl reduction of 3-fluoro-2-oxopropyl 4-methylphenyl sulphoxide are described.Keywords
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