Sulfonamide Ligands Attained Through Opening of Saccharin Derivatives

Literature N ‐alkylsaccharins (saccharin‐R 2 ) have been shown in some cases to be O ‐alkylated regioisomers by crystallography (3 structures). The genuine former species react with ( S )‐H 2 NCHR 1 CH 2 OH at 101 °C in dioxane to provide 1,2‐C 6 H 4 (CONHCHR 1 CH 2 OH)(SO 2 NHR 2 ) [R 1 = H, Me, i Pr, Bn, (CH 2 ) 2 SMe; R 2 = Bn, i Pr, CHPh 2 , CHMePh]. The ( i Pr,Bn) compound is crystallographically characterised. If both R 1 and R 2 are sterically congested then reaction of the amino alcohol with the saccharin surrogate 1,2‐C 6 H 4 (CO 2 Me)(SO 2 NHR 2 ) is required. The saccharin‐derived alcohols are converted into the oxazolines 1,2‐C 6 H 4 (R 1 ‐oxazoline)(SO 2 NHR 2 ) (R 1 = H, Bn, Me, i Pr; R 2 = Bn, CHPh 2 , n Pr, i Pr, t Bu, CHMePh). The dibenzyl compound is crystallographically characterised. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)