Efficient synthesis of primary 2-aminothiols from 2-aminoalcohols and methyldithioacetate

Synthesis of chiral thiazoline ligands tethered to a sulfur function and first immobilization of a thiazoline‐ligand

“…Compound 8 was chosen as an example of sulfanyl‐thiazoline ligand, in which the chain bearing the sulfanyl group is placed in the 4‐position of the thiazoline. The synthesis was performed in two steps (thioacylation and intramolecular cyclization) starting from phenyldithioic methyl ester 7 and commercially available ( S )‐methioninol 8. The nonoptimized overall yield was 59% (Scheme ).…”

“…Thioamide 7 was prepared from dithiobenzoic acid methyl ester (420 mg, 2.5 mmol) and ( S )‐methioninol (338 mg, 2.5 mmol) according to the procedure described in 8. Purification by column chromatography (EtOAc/pentane: 60/40, R f = 0.61 in UV) yielded 365 mg (1.43 mmol, 57%) of the title compound as a viscous yellow oil.…”

Aziridines Ring Opening by Silyl Chalcogenides: a Stereoselective Access to Polyfunctionalized Molecules as Precursor of Sulfurated and Selenated Heterocycles

“…Yield: 49% (determined by NMR). 1 21.7, 22.0, 23.0, 24.9, 21.5, 43.7, 56.4, 127.6, 129.5, 137.7, 142.9. 77 Se NMR (38 MHz, CDCl 3 ) -93.2.…”

“…77 Se NMR (38 MHz, CDCl 3 ) -93.2. N,N'-((2S,2'S)-Diselanediylbis(4-methylpentane-2,1-diyl))bis(4-methylbenzenesulfonamide) (8b) 1 21.5, 21.7, 22.8, 24.5, 37.2, 43.7, 52.4, 127.2, 129.7, 137.9, 143.4. 77 Se NMR (38 MHz, CDCl 3 ): 282.3.…”

“…4 2-Aminoalcohols represent the starting reagents used in most of the procedures described to access to 1,2-aminothiols, and generally the methods for their synthesis require a multistep sequence, such as the Mitsunobu reaction. 1,5 Other procedures, based on the ring opening of five membered N,S-heterocycles are reported. 5b Aziridines and thiiranes have been described as well in the reaction of sulfur or nitrogen heterocycles to synthesize β-amino thiols.…”