Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.

Selective reactions on structures of high complexity can move beyond the mind's eye and proof-of-principle. Enhanced understanding of noncovalent interactions and their interdependence, revealed through analysis of multiple parameters, should accelerate the discovery of efficient reactions in highly complex molecular environments.

[1]  J. Knowles,et al.  Enzyme catalysis: not different, just better , 1991, Nature.

[2]  W. Thiel.  Computational catalysis--past, present, and future. , 2014, Angewandte Chemie.

[3]  Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity , 2016, ACS central science.

[4]  M. Francis,et al.  Transition metal catalyzed methods for site-selective protein modification. , 2006, Current opinion in chemical biology.

[5]  Sławomir Janusz Grabowski,et al.  What is the covalency of hydrogen bonding? , 2011, Chemical reviews.

[6]  Hiromasa Kiyota,et al.  Natural taxanes: developments since 1828. , 2011, Chemical reviews.

[7]  Andrew J. Neel,et al.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion. , 2016, Journal of the American Chemical Society.

[8]  Martin D. Burke,et al.  Electronic Tuning of Site-Selectivity , 2012, Nature chemistry.

[9]  Walter Thiel,et al.  Computational Catalysis — Past, Present, and Future , 2014 .

[10]  G. Huisman,et al.  Engineering the third wave of biocatalysis , 2012, Nature.

[11]  M. White.  Adding Aliphatic C–H Bond Oxidations to Synthesis , 2012, Science.

[12]  Jean-Philip Piquemal,et al.  NCIPLOT: a program for plotting non-covalent interaction regions. , 2011, Journal of chemical theory and computation.

[13]  R. Breslow,et al.  An artificial cytochrome P450 that hydroxylates unactivated carbons with regio- and stereoselectivity and useful catalytic turnovers. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[14]  Eric N. Jacobsen,et al.  Attractive noncovalent interactions in asymmetric catalysis: Links between enzymes and small molecule catalysts , 2010, Proceedings of the National Academy of Sciences.

[15]  John F. Hartwig,et al.  A Simple, Multidimensional Approach to High-Throughput Discovery of Catalytic Reactions , 2011, Science.

[16]  Scott J. Miller,et al.  X-ray Crystal Structure of Teicoplanin A2-2 Bound to a Catalytic Peptide Sequence via the Carrier Protein Strategy , 2014, The Journal of organic chemistry.

[17]  F. Dean Toste,et al.  A data-intensive approach to mechanistic elucidation applied to chiral anion catalysis , 2015, Science.

[18]  E. Jacobsen,et al.  Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement , 2016, ACS central science.

[19]  Robert M. Long,et al.  Taxol Biosynthesis and Molecular Genetics , 2006, Phytochemistry Reviews.

[20]  Scott J. Miller,et al.  Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts. , 2006, Angewandte Chemie.

[21]  Robert J. Phipps,et al.  Harnessing non-covalent interactions to exert control over regioselectivity and site-selectivity in catalytic reactions , 2016, Chemical science.

[22]  Robert J. Phipps,et al.  A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes , 2013, Proceedings of the National Academy of Sciences.

[23]  K. Sharpless,et al.  Searching for new reactivity (Nobel lecture). , 2002, Angewandte Chemie.

[24]  Scott J. Miller,et al.  Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation , 2012, Nature chemistry.

[25]  P. Schreiner,et al.  London dispersion in molecular chemistry--reconsidering steric effects. , 2015, Angewandte Chemie.

[26]  Anat Milo,et al.  Developing a Modern Approach To Account for Steric Effects in Hammett-Type Correlations. , 2016, Journal of the American Chemical Society.

[27]  M. Kozlowski,et al.  Rapid quantification of the activating effects of hydrogen-bonding catalysts with a colorimetric sensor. , 2012, Journal of the American Chemical Society.

[28]  Scott J. Miller,et al.  Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: an approach to kinetic resolution of secondary alcohols of broad structural scope. , 2001, Journal of the American Chemical Society.

[29]  Ryoji Noyori Prof..  Asymmetric Catalysis: Science and Opportunities (Nobel Lecture) , 2002 .

[30]  Qi-Lin Zhou,et al.  Privileged chiral ligands and catalysts , 2011 .

[31]  Christopher K Prier,et al.  Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated Serendipity , 2011, Science.

[32]  Jinhua J. Song,et al.  The Growing Impact of Catalysis in the Pharmaceutical Industry , 2011 .

[33]  G. Whitesides,et al.  Complexity in chemistry. , 1999, Science.

[34]  E. Jacobsen,et al.  Thiourea-catalysed ring opening of episulfonium ions with indole derivatives by means of stabilising, non-covalent interactions , 2012, Nature Chemistry.

[35]  F. Toste,et al.  Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer. , 2016, Journal of the American Chemical Society.

[36]  Ryoji Noyori,et al.  Asymmetric catalysis: science and opportunities (Nobel lecture). , 2002, Angewandte Chemie.

[37]  P. Baran,et al.  If C—H Bonds Could Talk: Selective C—H Bond Oxidation. , 2011 .

[38]  E. Jacobsen,et al.  Privileged Chiral Catalysts , 2003, Science.

[39]  Scott J. Miller,et al.  Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin. , 2013, Journal of the American Chemical Society.

[40]  David M. Kaphan,et al.  A supramolecular microenvironment strategy for transition metal catalysis , 2015, Science.

[41]  T. Mei,et al.  Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids. , 2013, Journal of the American Chemical Society.

[42]  Anat Milo,et al.  Interrogating selectivity in catalysis using molecular vibrations , 2014, Nature.

[43]  Scott J. Miller,et al.  Chemical tailoring of teicoplanin with site-selective reactions. , 2013, Journal of the American Chemical Society.

[44]  Qi‐Lin Zhou.  Privileged Chiral Ligands and Catalysts: ZHOU:PRIVILEGED CATALYSTS O-BK , 2011 .

[45]  Anat Milo,et al.  The Development of Multidimensional Analysis Tools for Asymmetric Catalysis and Beyond. , 2016, Accounts of chemical research.

[46]  G. L. Hamilton,et al.  The progression of chiral anions from concepts to applications in asymmetric catalysis. , 2012, Nature chemistry.

[47]  P. Baran,et al.  Two-Phase Synthesis of (−)-Taxuyunnanine D , 2014, Journal of the American Chemical Society.

[48]  Robert J. Phipps,et al.  Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols. , 2013, Journal of the American Chemical Society.

[49]  Andrew J. Neel,et al.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids. , 2013, Journal of the American Chemical Society.

[50]  Shane W. Krska,et al.  The medicinal chemist's toolbox for late stage functionalization of drug-like molecules. , 2016, Chemical Society reviews.

[51]  Michel Dupuis,et al.  Toward molecular catalysts by computer. , 2015, Accounts of chemical research.