Base-catalyzed inversion of chiral sulfur centers. A computational study

David Balcells, Feliu Maseras, Noureddine Khiar

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)


A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe3 can catalyze the racemization. The base-catalyzed inversion of SO(CI)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.
Original languageEnglish
Pages (from-to)2197-2200
JournalOrganic Letters
Issue number13
Publication statusPublished - 24 Jun 2004


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