209787-96-2Relevant academic research and scientific papers
Sulfenate substitution as a complement and alternative to sulfoxidation in the diastereoselective preparation of chiral β-substituted β-amino sulfoxides
S?derman, Stefan C.,Schwan, Adrian L.
, p. 1638 - 1649 (2013/03/28)
Building from a previous communication, the reaction of sulfenate anions with chiral N-Boc-protected β-substituted β-amino iodides was evaluated as a conceptually different synthetic approach to chiral β-substituted β-amino sulfoxides. Using arenesulfenat
The diastereoselective alkylation of arenesulfenate anions using homochiral electrophiles
Soederman, Stefan C.,Schwan, Adrian L.
, p. 4192 - 4195 (2011/10/08)
A series of Boc-protected β-amino sulfoxides were prepared by the reaction of arenesulfenate anions with chiral Boc-protected β-amino iodides. The stereoselective substitution reaction is believed to arise through precoordination of the sulfenate counteri
Chiral β-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations
Lewanowicz,Lipinski,Siedlecka,Skarzewski,Baert
, p. 6571 - 6586 (2007/10/03)
Enantiomerically pure u and l β-amino sulfoxides have been easily obtained from the respective homochiral α-amino alcohols. The absolute configuration at the created stereogenic centre was assigned by CD spectra and by X-ray analysis. Conformational analysis of the title compounds was carried out using quantum chemical energy-geometry optimization. Thus established conformational behavior explained the strongly configuration dependent NMR spectral patterns observed for the u and l diastereomers.
