Quantum Mechanical Models Correlating Structure with Selectivity: Predicting the Enantioselectivity of β-Amino Alcohol Catalysts in Aldehyde Alkylation

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Abstract
Quantitative structure selectivity relationship (QSSR) models are described that provide consistently reliable predictions for the asymmetric addition of Et2Zn to PhCHO catalyzed by β-amino alcohols. Statistically valid two-variable linear regression models that correlate the structures of the chiral catalysts with their enantioselectivities are obtained from three-dimensional physical property grids. The strength of the present method is that statistical models obtained from a small set of experimentally determined selectivities and relatively simple theoretical calculations yield selectivity predictions that are as accurate as those derived from higher-level calculations of transition-structure energies. Only minutes of computing time are required. Simple models are obtained which permit straightforward physical interpretation and generate realistic predictions.