Three-Dimensional Correlation of Steric and Electronic Free Energy Relationships Guides Asymmetric Propargylation

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Science  30 Sep 2011:
Vol. 333, Issue 6051, pp. 1875-1878
DOI: 10.1126/science.1206997

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Chemical reaction outcomes are often rationalized on the basis of independent analyses of steric and electronic effects. We applied three-dimensional free energy relationships correlating steric and electronic effects to design and optimize a ligand class for the enantioselective Nozaki-Hiyama-Kishi propargylation of ketones. The resultant mathematical model describing the steric and electronic parameter relationship is highly reliant on the synergistic interactions of these two effects.

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