Authors: Sosale Chandrasekhar
A comprehensive analysis of the available evidence on the Soai reaction leads to remarkable conclusions, concerning both the rate determining transition state and the nature of the catalyst species. Thus, autocatalysis per se cannot account for the experimental observations. In fact, the irreversible formation of a heterochiral, non—reacting species from the alcohol product, as also the formation of a dimeric species from the aldehyde substrate are indicated: The former enhances the e.e. of the alcohol that is both product and catalyst, while the latter accounts for the observed rate laws. Furthermore, the non—involvement of the dialkyl zinc species in the rate determining step, and its nucleophilic addition to aldehyde with high enantioselectivity are also indicated. Indeed, it appears there is no other way to account for the remarkable experimental findings on one of the most spectacular discoveries in chemistry.
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