Nitroepoxide ring opening with thionucleophiles in water: Synthesis of α-xanthyl ketones, β-keto sulfones and β-keto sulfonic acids
Nitroepoxide ring opening with thionucleophiles such as potassium xanthates, sodium aryl sulfinates and sodium bisulfite in water is investigated. It provides a direct and green route for the synthesis of α-xanthyl-α-aryl-2-propanones (P2P-xanthate derivatives), β-keto sulfones and β-keto sulfonic acids. High to excellent yields, performing the reaction in water under catalyst-free conditions, and easy work-up are the main advantages of this protocol.
Chemoselective one-pot synthesis of β-keto sulfones from ketones
A practical method to synthesize substituted β-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an α-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of β-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.
Rawat, Vikas S.,Reddy, Perla L. M.,Sreedhar, Bojja
p. 5165 - 5168
(2014/01/23)
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