title: Quantum mechanical models correlating structure with selectivity: predicting the enantioselectivity of beta-amino alcohol catalysts in aldehyde alkylation.
abstract: Quantitative structure selectivity relationship (QSSR) models are described that provide consistently reliable predictions for the asymmetric addition of Et2Zn to PhCHO catalyzed by beta-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.
authors.affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. marisa@sas.upenn.edu
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
authors.forename: Steven L
authors.initials: SL
authors.lastname: Dixon
authors.forename: Manoranjan
authors.initials: M
authors.lastname: Panda
authors.forename: Giorgio
authors.initials: G
authors.lastname: Lauri
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D013816:Thermodynamics
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols