125553-49-3Relevant academic research and scientific papers
Substituent Effect on the Enantiomer-Differentiating Reaction of Lithiomethyl p-Tolyl Sulfoxide with Meta- or Para-Substituted (R)-(-)-Menthyl Benzoates
Kunieda, Norio,Nakanishi, Takeshi,Kinoshita, Masayoshi
, p. 2229 - 2234 (1989)
Treatment of (R)-(-)-menthyl benzoates, which have a variety of meta- or para-substituents, with 2 equivalents of racemic lithiomethyl p-tolyl sulfoxide displays the feature of an enantiomer-differentiating reaction, affording the corresponding optically active β-keto sulfoxides.The degree and the direction of enantioselectivity were affected by the nature of the substituent on benzene ring.The electron-releasing substituents trend to increase the percente.e. value.The reversal in the configuration with the variation in the substituent which has a high electron-withdrawing p-CN group was also observed.The R/S values thus obtained gave a good correlation with Hammett's ? values (γ = 0.975), affording a negative straight line. based on these observations, a plausible stereochemical course of this reaction has been discussed.
Highly enantiomeric purity conversion of α-sulfinyl oximes and α-sulfinyl hydrazones to the corresponding β-keto sulfoxides with butyltriphenylphosphonium periodate (BUTPPPI)
Hajipour,Ruoho
, p. 2653 - 2657 (2007/10/03)
Butyltriphenylphosphonium periodate (Ph3P+BuIO 4-)1 is readily prepared as a white solid from butyltriphenylphosphonium chloride, performs conversion of α-sulfinyl oximes (2) and α-sulfinyl hydrazones (4) to the
1,3-Asymmetric Induction in the Reduction of α-Alkyl β-Ketosulfoxides with DIBAL/ZnBr2
Barros, David,Carreno, M. Carmen,Ruano, Jose L. Garcia,Maestro, M. Carmen
, p. 2733 - 2736 (2007/10/02)
The highly stereoselective reduction of chiral α-alkyl β-ketosulfoxides with DIBAL/ZnBr2 is governed by the configuration at the sulfur (1,3-induction) and not by that of the C-α (1,2-induction) as it has been previously reported.This fact considerably in
