145679-46-5Relevant academic research and scientific papers
Cyclic sulfonimidates by dynamic diastereomer-differentiating cyclisation: Large-scale synthesis and mechanistic studies
Reggelin, Michael,Junker, Bernd
, p. 1232 - 1239 (2007/10/03)
A dynamic diastereomer differentiating cyclisation is the key step in a new large-scale synthesis of both enantiomers of the cyclic sulfonimidates 1 (Aldrich no. 54099-4) and ent-1 (Aldrich no. 54412-4). These are valuable starting materials in the asymmetric synthesis of chiral oxa- and azaheterocyclic compounds. NMR spectroscopic studies on the reacting system reveal N-chloro sulfinamides to be reactive intermediates in the oxidative chlorination of sulfinamides with tert-butyl hypochlorite and allow for the inspection of the configurational behaviour of the involved sulfonimidoyl chlorides and sulfonimidoyl bromides.
One-pot synthesis of (S)-4-isopropyl-2-p-toluene-4,5-dihydro-[1.2λ6,3]oxathiazole 2-Oxides: Efficient precursors of optically active sulfoximines
Reggelin, Michael,Weinberger, Heinz
, p. 6959 - 6962 (2007/10/02)
The title compounds were prepared from p-toluenesulfinyl chloride and (S)-O-trimethylsilyl valinol without isolation of intermediates. Key step in the synthesis is the fluoride-induced cyclisation of sulfonimidoyl chlorides yielding the crystalline sulfon
