Simple performic acid oxidation of acetylthio group to sulfonic acid and its application in syntheses of 2-substituted taurines

The first synthesis of optically active 1-substituted taurines

“…Optically active β-amino secondary alcohols are important key intermediates for synthesizing optically active 1-substituted taurines (see Scheme 1). First, optically active β-amino secondary alcohols 1 were protected with benzyl chloroformate to give 1-(benzyloxycarbonyl)amino-2-alkanols [benzyl N-(2-hydroxyalkyl) carbamates] 2, which were converted to the corresponding thioacetates 3 in a Mitsunobu displacement reaction using DEAD (diethyl azodicarboxylate), triphenylphosphine, and thiolacetic acid [11][12][13], in which a Walden inversion occurs. HPLC analysis on a chiral column indicated that the benzyl N-(2-hydroxyalkyl) carbamates 2 occurred in a complete configurational inversion to yield the optically active corresponding thioacetates 3 in the Mitsunobu reaction except for some acetate by-products.…”

“…The free 1-substituted taurines 4 can also be obtained by treatment of 1-substituted N-benzyloxycarbonyl protected taurines 5 with formic acid under refluxing conditions. In general, the benzyloxycarbonyl group is removed with Pd/C under hydrogen atmosphere [11]. However, the current method can avoid hydrogenolytic cleavage on the benzylic position for products 5a.…”

Synthesis of α- and β-Substituted Aminoethane Sulfonamide Arginine-Glycine Mimics

“…2000, 1219Ϫ1228 1220 duction of its in situ prepared mixed anhydride. [10] Alcohol 10 was then transformed into its mesylate 11 in 80% yield, from which the mesylate moiety was displaced in a substitution reaction using cesium thioacetate [11] to afford the key thioacetate 12 in 69% yield. After conversion into the corresponding sulfinyl chloride 13 by treatment of this synthon with sulfuryl chloride and acetic anhydride, a coupling reaction with an amine was carried out to obtain the desired sulfinamide, which was immediately oxidized to the corresponding sulfonamide.…”

A Simple Synthesis of Nβ-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of Nβ-Fmoc/Z-Amino Alkyl Sulfonic Acids

“…Among the various methods available for their preparation, direct conversion of amino alcohols via sulfite displacement 32 and performic acid oxidation of Boc/Z-b-amino thioacetates are attractive. 33 Gude et al, prepared a Boc-NH-Xaa-y[SO 2 Cl] series via betaines obtained from mesylates of Boc-b-amino alcohols. 34 Liskamp's group reported the synthesis of N-Fmoc-b-aminoethanesulfonyl chlorides via the oxidation of N-Fmoc-bamino thioacetates generated by Cs 2 CO 3 -promoted reaction of N-Fmoc-b-amino alkyl mesylate with thioacetic acid.…”