Synthetic Applications of π-Electron-Deficient Sulfones

Abstract

The use of π-electron-deficient aryl sulfones, especially 3,5-bis(trifluoromethyl) phenyl alkyl sulfones (BTFP-sulfones) as soft nucleophiles, as caboxylic acid protecting group and in Julia–Kocienski olefination reactions is described. In the case of α-(arylsulfonyl)acetates dialkylation, reactions are performed under phase-transfer analysis (PTC) conditions using K ₂ CO ₃ as base. Esters derived from 2-(arylsulfonyl)ethanol can be deprotected using aqueous NaHCO ₃ . Alkyl BTFP sulfones are coupled with carbonyl compounds using KOH or P4-t-Bu as bases to give the corresponding alkenes after Smiles rearrangement.

keywords:

• Aconitates;
• elimination;
• olefination;
• protecting groups;
• stilbenoids;
• sulfones