Experimental and theoretical study of reduction reaction of Cis and Trans 4-tert-butyl-2-X-ciclohexanone (X = F and Cl) with N-selectride

The study of diastereoselective in reduction reaction of 4-tert-butyl-2-X-ciclohexanone (X=F and Cl) with N-Selectride were obtained by means of experimental results and theoretical calculations. For substituents in axial position in carbon 2 was obtained the equatorial alcohol and theoretical calculations of transition state showed that approximation of reducing reagent by axial face is favorable than approximation by equatorial face. However, for substituents in equatorial position was obtained the axial alcohol because the approximation of reducing by equatorial face is favorable than approximation by axial face. The electronic effects like Cieplak model and higher ring torsion angle were used to explain the experimental results observed. (author)