151648-26-9Relevant academic research and scientific papers
Synthesis, Structural Characterization and Stereocontrolled Degradation of 2-Azacephams
Herak, Jure J.,Vinkovic, Mladen,Mandic, Zorica,Lukic, Irena,Tomic, Mirjana,Kovacevic, Mice
, p. 1605 - 1612 (1994)
The enantiomerically pure substituted 2-azacephams 5 were synthesized by intramolecular cyclization of sulfinamides 4.Their absolute configurations were confirmed by X-ray crystal structure determination of (5R,6R)-4-benzyl-2-isopropylidene-5-oxo-5-thia-1
Chiral Sulfinyl Chlorides as Intermediates in Interconversion of 4-Oxoazetidine-2-sulfinic Acid Derivatives
Herak, Jure J.
, p. 393 - 398 (2007/10/02)
Stereochemically pure methylsulfinates 3 and benzylsulfinamides 4 are readily epimerized in the presence of hydrogen chloride and at the same time they can be transformed by sulfinate-sulfinamide interconversion.Formation of sulfinyl chlorides 2 as intermediates and their epimerization by rapid chloride anion exchange at sulfur atom is proposed.The equilibrated ratio between epimers 2a and 2b determines the enantioselectivity of these processes.
4-Oxazetidine-2-sulphinic Acid Derivatives; Preparation and Determination of Configuration by 1H Nuclear Magnetic Resonance Spectroscopy
Herak, Jure J.,Vinkovic, Mladen,Kojic-Prodic, Biserka
, p. 1201 - 1226 (2007/10/02)
Reaction of 4-oxoazetidine-2-sulphinyl chlorides 1 with amines gave diastereoisomeric sulphinamides 6 and 7.Oxidation of the isomers 6 and 7 afforded the corresponding sulphonamides 12.From the reaction of the sulphinyl chlorides 1 with 2-mercaptobenzothiazole, disulphides 9a, 9b and 10 were isolated.Treatment of sulphinates 4a and 5a with aluminum trichlorideanisole afforded acids 4e and 5e, which can be converted into mixed anhydrides 4f and 5f.The absolute configurations of the sulphinates 4 and 5 and sulphinamides 6 and 7 were assigned on the basis of 1H NMRspectroscopic studies and verified by X-ray structure analysis of sulphinate 4b.
