A Convenient Synthesis of 3-Fluorinated 2-Oxopropyl Sulphoxides from Fluorinated Lithium Acetates and 1-Lithioalkyl Sulphoxides

Pierfrancesco Bravo; Elena Piovosi; Giuseppe Resnati

doi:10.1055/s-1986-31714

Synthesis 1986; 1986(7): 579-582
DOI: 10.1055/s-1986-31714

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A Convenient Synthesis of 3-Fluorinated 2-Oxopropyl Sulphoxides from Fluorinated Lithium Acetates and 1-Lithioalkyl Sulphoxides

Pierfrancesco Bravo^* , Elena Piovosi, Giuseppe Resnati

^*C.N.R. - Centro Studio Sostanze Organiche Naturali, Dipartimento di Chimica, Politecnico di Milano, Piazza Leonardo da Vinci 32, I-20133 Milano, Italy

Abstract

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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.

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