13576-16-4Relevant academic research and scientific papers
Direct asymmetric α-sulfamidation of α-branched aldehydes: A novel approach to enamine catalysis
Vogt, Henning,Baumann, Thomas,Nieger, Martin,Braese, Stefan
, p. 5315 - 5338 (2007/10/03)
Proline-catalysed reactions between α-branched aldehydes and sulfonyl azides provide scalemic configurationally stabilised α-sulfamidated products with ee values of up to 86%. The reactions can also be carried out in a one-pot fashion, with catalyst, alde
Sulfamidation of 2-arylaldehydes and ketones with chloramine-T
Baumann, Thomas,Bachle, Michael,Brase, Stefan
, p. 3797 - 3800 (2007/10/03)
A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either α-sulfamidation in the case of aromat
Stereoselective addition of α-sulfinyl carbanions to N-p-tolylsulfinylketimines: Synthesis of optically pure 1,2,2′-trialkyl-2- aminoethanols
Garcia Ruano, Jose L.,Aleman, Jose,Del Prado, Miriam,Fernandez, Inmaculada
, p. 4454 - 4463 (2007/10/03)
The reactions of lithium carbanions derived from both enantiomers of methyl (1) and ethyl p-tolyl sulfoxide (2) with (S)-N-arylsulfinylketimines 3 and 4 took place in a highly stereoselective manner and good isolated yields. The configuration of the carbon bonded to nitrogen relies exclusively on the N-sulfinylimine configuration. When ethyl p-tolyl sulfoxide (2) is use as nucleophile, two chiral centers are created simultaneously, where the configuration of the carbon bonded to the sulfur is mainly controlled by 2. The asymmetric induction increases with the temperature, being total at room temperature in the case of the matched pair of reactants. A non-oxidative Pummerer reaction on the obtained aminosulfoxides allows a straightforward synthesis of optically pure 1,2-ethanolamines with one or two chiral centers, including amino alcohols with a bulky quaternary carbon bonded to the amine group.
