6533b824fe1ef96bd128161b
RESEARCH PRODUCT
Cyclic Sulfonimidates by Dynamic Diastereomer-Differentiating Cyclisation: Large-Scale Synthesis and Mechanistic Studies
Michael ReggelinJunker Berndsubject
chemistry.chemical_compoundChemistryOrganic ChemistryReactive intermediateEnantioselective synthesisDiastereomerHypochloriteOrganic chemistryGeneral ChemistryNuclear magnetic resonance spectroscopyEnantiomerCatalysisChiral resolutiondescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-03-16 | Chemistry |