Novel route to racemization of sulfoxides

  title={Novel route to racemization of sulfoxides},
  author={Giorgio Modena and U. Quintily and Gianfranco Scorrano},
  journal={Journal of the American Chemical Society},
27 Citations
Dual In-Tether Chiral Centers Modulate Peptide Helicity.
In this work, peptides were constrained into helical conformations via the synergistic effects of dual in-tether chiral centers through a pentapeptide minimalistic model to provide an on-Tether modification site that does not interrupt the secondary structure of the peptide.
Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity
The preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings with properties with respect to ring size, sulfur position, oxidation state, and stereochemistry show a propensity to induce α-helicity.
Unexpected reactions of Grignard reagents with selected β-carboalkoxy substituted sulfinate esters
A series of six-membered rings bearing cis oriented vicinal carboxylate and sulfinate esters were treated with Grignard reagents with the intention of transforming them to β-carboalkoxy substituted
Configurational Stability of Optically Active Dichloromethyl p-Tolyl Sulfoxide and Its Anionic Species: Experimental and Theoretical Study
Racemization of optically active dichloromethyl p-tolyl sulfoxide took place at −78°C in the presence of potassium bis(trimethylsilyl)amide (KHMDS), while the same racemization did not occur under
Chiral sulfoxides in the enantioselective allylation of aldehydes with allyltrichlorosilane: a kinetic study.
The mechanism of the allylation of aldehydes in the presence of allyltrichlorosilane employing the commercially available (R)-methyl p-tolyl sulfoxide as a Lewis base has been investigated and indicates that the reaction proceeds through a dissociative pathway in which an octahedral cationic complex with two sulfoxides is involved.
Sulfoxides in the allylation of aldehydes in the presence of silicon tetrachloride and allyltributylstannane
SiCl4 can be conveniently activated by catalytic amounts of dimethyl sulfoxide or other readily-available sulfoxides for the allylation of aromatic, hetero-aromatic and unsaturated aldehydes in the
Origin of the stereoselectivity in (ethoxycarbonyl)-, cyano-, and phenyl-substituted (arylsulfinyl)methyl radicals
An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfinyl)methyl radicals is presented, based on experimental results and semiempirical
Contrasting pathways for the directed homogeneous hydrogenation of vinyl sulfoxides and vinyl sulfones
Rh-complex catalysed directed hydrogenation of (α-hydroxyalkyl)vinyl sulfones follows the same stereochemical course as the corresponding acrylates, via HO-coordination; hydrogenation of the related