Literature DB >> 20486656

Linear free-energy relationship analysis of a catalytic desymmetrization reaction of a diarylmethane-bis(phenol).

Jeffrey L Gustafson1, Matthew S Sigman, Scott J Miller.   

Abstract

Linear free-energy relationships have been found for enantioselectivity and various steric parameters in an enantioselective desymmetrization of symmetrical bis(phenol) substrates. The potential origin of this observation and the role of different steric parameters are discussed.

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Year:  2010        PMID: 20486656      PMCID: PMC2886716          DOI: 10.1021/ol100927m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

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5.  Remote desymmetrization at near-nanometer group separation catalyzed by a miniaturized enzyme mimic.

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6.  Quantitatively correlating the effect of ligand-substituent size in asymmetric catalysis using linear free energy relationships.

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7.  Solvent effects on stereoselectivity: more than just an environment.

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8.  Examination of the role of Taft-type steric parameters in asymmetric catalysis.

Authors:  Matthew S Sigman; Jeremie J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

Review 9.  Combinatorial libraries of transition-metal complexes, catalysts and materials.

Authors:  M B Francis; T F Jamison; E N Jacobsen
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10.  A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis(phenol).

Authors:  Chad A Lewis; Jeffrey L Gustafson; Anna Chiu; Jaume Balsells; David Pollard; Jerry Murry; Robert A Reamer; Karl B Hansen; Scott J Miller
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

  10 in total
  15 in total

1.  Multidimensional steric parameters in the analysis of asymmetric catalytic reactions.

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5.  Kinetic isotope effects in asymmetric reactions.

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6.  Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst.

Authors:  Alex J Chinn; Byoungmoo Kim; Yongseok Kwon; Scott J Miller
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Review 7.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

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8.  Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.

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Journal:  ACS Catal       Date:  2018-09-13       Impact factor: 13.084

9.  Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.

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Review 10.  Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

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Journal:  Chem Rev       Date:  2019-12-30       Impact factor: 60.622

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