Chernykh, Anton V. published the artcileA stereochemical journey around spirocyclic glutamic acid analogs, Name: (S)-2-Methylpropane-2-sulfinamide, the main research area is glutamic acid spirocyclic analog library enantioselective diastereoselective regioselective synthesis; silylated hydroxymethyl cyclobutanone Tebbe olefination; dichloroketene addition Meinwald oxirane rearrangement ketone Strecker reaction; chiral auxiliary Ellman sulfinamide glutamic acid; crystal structure spirocycle Helicobacter pylori glutamate racemase inhibitor.
A practical divergent synthetic approach is reported for the library of regio- and stereoisomers of glutamic acid analogs built on the spiro[3.3]heptane scaffold. Formation of the spirocyclic scaffold was achieved starting from a common precursor – an O-silylated 2-(hydroxymethyl)cyclobutanone derivative Its olefination required using the titanium-based Tebbe protocol since the standard Wittig reaction did not work with this particular substrate. The construction of the second cyclobutane ring of the spirocyclic system was achieved through either subsequent dichloroketene addition or Meinwald oxirane rearrangement as the key synthetic steps, depending on the substitution patterns in the target compounds (1,6- or 1,5-, resp.). Further modified Strecker reaction of the resulting racemic spirocyclic ketones with the Ellman′s sulfinamide as a chiral auxiliary had low to moderate diastereoselectivity; nevertheless, all stereoisomers were isolated in pure form via chromatog. separation, and their absolute configuration was confirmed by X-ray crystallog. Members of the library were tested for the inhibitory activity against H. pylori glutamate racemase.
Organic & Biomolecular Chemistry published new progress about Chiral auxiliary. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Name: (S)-2-Methylpropane-2-sulfinamide.
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