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Quantitatively Correlating the Effect of Ligand‐Substituent Size in Asymmetric Catalysis Using Linear Free Energy Relationships
Author(s) -
Miller Jeremie J.,
Sigman Matthew S.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704257
Subject(s) - substituent , steric effects , ligand (biochemistry) , chemistry , bromide , enantiomer , modular design , product (mathematics) , catalysis , computational chemistry , medicinal chemistry , stereochemistry , computer science , mathematics , organic chemistry , biochemistry , receptor , geometry , operating system
Is bigger better? By systematically evaluating the size of the substituent G in a modular ligand (see picture), a linear free energy relationship was observed relating the product enantiomeric ratio to steric parameters developed by Charton. The reaction studied was the addition of allyl bromide to three different carbonyl substrates.