1,2-asymmetric induction in carbonyl compounds: a computational study
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Date
2019
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University of New Brunswick
Abstract
In asymmetric synthesis, it is important to reliably predict the major stereoisomeric product of a reaction. One such reaction is the nucleophilic addition to a carbonyl compound featuring an adjacent chiral carbon. Several reaction models exist in literature to predict the facial selectivity of these reactions. These models provide simple visual drawings to quickly predict the major product of such a reaction without requiring exhaustive quantum mechanical calculations. These models are used on a daily basis, and some models perform better than others, making it valuable to investigate which ones are the most effective.
For the first time in this thesis, high-level computations have been performed on all of the literature models to verify their efficacy. The results of this thesis offers a definitive answer that the Felkin-Anh and Wintner models are the most effective, and that bent bond theory offers an interesting insight on the mechanics of these reactions.