A Michael Route to Acetals and Thioacetals: Preparation of Acetals (Thioacetals) of 2-Sulfonylacetaldehyde from Alkynyl and Other Unsaturated Aryl Sulfones

Sergio Cossu; Ottorino De Lucchi; Fabrizio Fabris; Roberto Ballini; Giovanna Bosica

doi:10.1055/s-1996-4406

Synthesis 1996; 1996(12): 1481-1484
DOI: 10.1055/s-1996-4406

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A Michael Route to Acetals and Thioacetals: Preparation of Acetals (Thioacetals) of 2-Sulfonylacetaldehyde from Alkynyl and Other Unsaturated Aryl Sulfones

Sergio Cossu, Ottorino De Lucchi^* , Fabrizio Fabris, Roberto Ballini, Giovanna Bosica

^*Dipartimento di Chimica, Università Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy, Fax +415298517; E-mail delucchi@vega.unive.it

Abstract

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A simple protocol for the direct transformation of arylsulfonylalkynes 1, (Z)- and (E)-1,2-bis(phenylsulfonyl)ethylene (2), and (E)-1-chloro-2-phenylsulfonylethylene (3) into the acetals or thioacetals of acetyl sulfones is presented. It engages the NaH-catalyzed reaction of an alcohol or a thiol with 1-3 at room temperature for 2-12 hours. Emphasis is given to enantiopure C ₂ symmetric diols for the production of chiral building blocks to be used in asymmetric synthesis.

ethynyl tolylsulfone - 1,2-bis(phenylsulfonyl)ethylene - nucleophilic addition - acetals - acetyl sulfones

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