84229-01-6Relevant articles and documents
New Methods and Reagents in Organic Synthesis. 26. Reductive Desulfonylation of α-Sulfonylacetates
Kuo, Ying-Che,Aoyama, Toyohiko,Shioiri, Takayuki
, p. 2787 - 2792 (2007/10/02)
α-Acyl-benzylsulfonyldiazomethanes (2a-d) have been converted to α-benzylsulfonyl-α-substituted-acetic acids (7a-d) by means of the Wolff rearrangement.Reductive removal of the benzylsulfonyl group of 7b-d can be achieved by the use of sodium-ethanol in tetrahydrofuran. α-Benzylsulfonyl-α-substituted-propionic acids (9a-d), prepared from benzyl α-benzylsulfonyl-α-substituted-acetates (3a-d), were also debenzylsulfonylated under similar reductive conditions.The overall process, in combination with the Arndt-Eistert synthesis of α-sulfonylacetates from acyl chlorides and benzylsulfonyldiazomethane (1), provides a new, safe method for the homologation of carboxylic acids.Keywords-reductive desulfonylation; Wolff rearrangement; sodium amalgam reduction; catalytic debenzylation; sodium-ethanol reduction; methylation; α-substituted propionic acid; α-sulfonylacetate