Investigation of the hydroboration–oxidation of hindered cycloalkenes via molecular mechanics calculations

Abstract

Computational procedures based on molecular mechanics calculations have been devised for investigating the outcome of multi-centre stereoselective reactions. The algorithms, one of which requires no knowledge of transition state geometry, were tested against the known product distributions arising from hydroboration–oxidation experiments on a range of sterically hindered cyclohexenes. The first algorithm performs satisfactorily provided that all possible directions of reagent approach to the reaction site are significantly hindered, whilst molecular mechanics calculations of model transition state structures provide good results whether the reaction site is crowded or not.