Computational study of Rh(I)-Catalyzed Cycloaddition–Fragmentation of N-cyclopropylacrylamides

[1]  Guangbin Dong,et al.  Fused-Ring Formation by an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes. , 2018, Angewandte Chemie.

[2]  Cheng-Hang Liu,et al.  Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton. , 2017, Angewandte Chemie.

[3]  Juan Li,et al.  Mechanism of Rh(III)-catalyzed cyclopropanation using N-enoxyphthalimides and alkenes: Insights from DFT calculations , 2016 .

[4]  Guangbin Dong,et al.  Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis. , 2016, Chemistry.

[5]  M. Murakami,et al.  Potential of Metal-Catalyzed C-C Single Bond Cleavage for Organic Synthesis. , 2016, Journal of the American Chemical Society.

[6]  J. Bower,et al.  New Initiation Modes for Directed Carbonylative C–C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes , 2016, Journal of the American Chemical Society.

[7]  Zhi‐Xiang Yu,et al.  Formal Synthesis of Gracilamine Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-Vinylcyclopropanes and CO. , 2016, The Journal of organic chemistry.

[8]  J. Bower,et al.  Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system , 2016 .

[9]  Q. Peng,et al.  Computational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization , 2016, Nature Communications.

[10]  Xin Yang,et al.  Computational Mechanism Study of Catalyst-Dependent Competitive 1,2-C→C, −O→C, and −N→C Migrations from β-Methylene-β-silyloxy-β-amido-α-diazoacetate: Insight into the Origins of Chemoselectivity , 2016 .

[11]  Yun-Dong Wu,et al.  Mechanism of Ni-NHC Catalyzed Hydrogenolysis of Aryl Ethers: Roles of the Excess Base , 2016 .

[12]  F. Bickelhaupt,et al.  Factors controlling β-elimination reactions in group 10 metal complexes. , 2015, Chemistry.

[13]  Zhi‐Xiang Yu,et al.  Rhodium-catalyzed [5 + 2 + 1] cycloaddition of ene-vinylcyclopropanes and CO: reaction design, development, application in natural product synthesis, and inspiration for developing new reactions for synthesis of eight-membered carbocycles. , 2015, Accounts of chemical research.

[14]  T. Sperger,et al.  Computational Studies of Synthetically Relevant Homogeneous Organometallic Catalysis Involving Ni, Pd, Ir, and Rh: An Overview of Commonly Employed DFT Methods and Mechanistic Insights. , 2015, Chemical reviews.

[15]  J. Bower,et al.  Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy , 2015, Journal of the American Chemical Society.

[16]  N. Cramer,et al.  Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals. , 2015, Chemical reviews.

[17]  Xu-Fei Fu,et al.  Rh(I)-catalyzed benzo/[7+1] cycloaddition of cyclopropyl-benzocyclobutenes and CO by merging thermal and metal-catalyzed C-C bond cleavages. , 2015, Chemistry.

[18]  Zhi‐Xiang Yu,et al.  Formal synthesis of (±)-galanthamine and (±)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO. , 2015, The Journal of organic chemistry.

[19]  J. Bower,et al.  Reversible C-C bond activation enables stereocontrol in Rh-catalyzed carbonylative cycloadditions of aminocyclopropanes. , 2015, Journal of the American Chemical Society.

[20]  Yuanzhi Xia,et al.  Catalyst-Controlled C–C σ Bond Cleavages in Metal Halide-Catalyzed Cycloisomerization of 3-Acylcyclopropenes via a Formal 1,1-Halometalation Mechanism: Insights from Quantum Chemical Calculations , 2015 .

[21]  K. Houk,et al.  Reactivity and Chemoselectivity of Allenes in Rh(I)-Catalyzed Intermolecular (5 + 2) Cycloadditions with Vinylcyclopropanes: Allene-Mediated Rhodacycle Formation Can Poison Rh(I)-Catalyzed Cycloadditions , 2014, Journal of the American Chemical Society.

[22]  F. Matthias Bickelhaupt,et al.  Controlling the oxidative addition of aryl halides to Au(I) , 2014, J. Comput. Chem..

[23]  K. Houk,et al.  Theoretical elucidation of the origins of substituent and strain effects on the rates of Diels-Alder reactions of 1,2,4,5-tetrazines. , 2014, Journal of the American Chemical Society.

[24]  N. Jiao,et al.  Recent advances in transition-metal-catalyzed functionalization of unstrained carbon-carbon bonds. , 2014, Chemical reviews.

[25]  Richard L. Lord,et al.  Switching the enantioselectivity in catalytic [4 + 1] cycloadditions by changing the metal center: principles of inverting the stereochemical preference of an asymmetric catalysis revealed by DFT calculations. , 2014, Journal of the American Chemical Society.

[26]  F. Bickelhaupt,et al.  The activation strain model and molecular orbital theory: understanding and designing chemical reactions. , 2014, Chemical Society reviews.

[27]  Guangbin Dong,et al.  Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems. , 2014, Organic chemistry frontiers : an international journal of organic chemistry.

[28]  K. Houk,et al.  Distortion/Interaction analysis reveals the origins of selectivities in iridium-catalyzed C-H borylation of substituted arenes and 5-membered heterocycles. , 2014, Journal of the American Chemical Society.

[29]  K. Houk,et al.  Mechanisms and origins of switchable chemoselectivity of Ni-catalyzed C(aryl)-O and C(acyl)-O activation of aryl esters with phosphine ligands. , 2014, Journal of the American Chemical Society.

[30]  Tao Shen,et al.  Selective C(sp2)-C(sp) bond cleavage: the nitrogenation of alkynes to amides. , 2013, Angewandte Chemie.

[31]  Zhi‐Xiang Yu,et al.  Vinylcyclopropane derivatives in transition-metal-catalyzed cycloadditions for the synthesis of carbocyclic compounds. , 2013, The Journal of organic chemistry.

[32]  J. Bower,et al.  Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones. , 2013, Journal of the American Chemical Society.

[33]  J. T. Njardarson,et al.  Recent Advances in the Metal-Catalyzed Ring Expansions of Three- and Four-Membered Rings , 2013 .

[34]  M. Baik,et al.  Stereoselective rhodium-catalyzed [3 + 2 + 1] carbocyclization of alkenylidenecyclopropanes with carbon monoxide: theoretical evidence for a trimethylenemethane metallacycle intermediate. , 2012, Journal of the American Chemical Society.

[35]  K. Houk,et al.  Ligand effects on rates and regioselectivities of Rh(I)-catalyzed (5 + 2) cycloadditions: a computational study of cyclooctadiene and dinaphthocyclooctatetraene as ligands. , 2012, Journal of the American Chemical Society.

[36]  Lantao Liu,et al.  Atom- and step-economical pathway to chiral benzobicyclo[2.2.2]octenones through carbon-carbon bond cleavage. , 2012, Angewandte Chemie.

[37]  F. Matthias Bickelhaupt,et al.  Alder‐ene reaction: Aromaticity and activation‐strain analysis , 2012, J. Comput. Chem..

[38]  Zhi‐Xiang Yu,et al.  Asymmetric Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter and density functional theory study of the origins of enantioselectivity. , 2012, Journal of the American Chemical Society.

[39]  Hu Li,et al.  Pyridinyl directed alkenylation with olefins via Rh(III)-catalyzed C-C bond cleavage of secondary arylmethanols. , 2011, Journal of the American Chemical Society.

[40]  N. Cramer,et al.  Cyclobutanes in catalysis. , 2011, Angewandte Chemie.

[41]  Zhi‐Xiang Yu,et al.  Enantioselective total synthesis of (+)-asteriscanolide via Rh(I)-catalyzed [(5+2)+1] reaction. , 2011, Chemical communications.

[42]  F. Bickelhaupt,et al.  Aromaticity and activation strain analysis of [3 + 2] cycloaddition reactions between group 14 heteroallenes and triple bonds. , 2011, The Journal of organic chemistry.

[43]  Zhi‐Xiang Yu,et al.  Density functional theory study of the mechanisms and stereochemistry of the Rh(I)-catalyzed intramolecular [3+2] cycloadditions of 1-ene- and 1-yne-vinylcyclopropanes. , 2011, Journal of the American Chemical Society.

[44]  Zhi‐Xiang Yu,et al.  Rh(I)-catalyzed formal [5 + 1]/[2 + 2 + 1] cycloaddition of 1-yne-vinylcyclopropanes and two CO units: one-step construction of multifunctional angular tricyclic 5/5/6 compounds. , 2011, Journal of the American Chemical Society.

[45]  F Matthias Bickelhaupt,et al.  The activation strain model of chemical reactivity. , 2010, Organic & biomolecular chemistry.

[46]  K. Houk,et al.  Electronic and steric control of regioselectivities in Rh(I)-catalyzed (5 + 2) cycloadditions: experiment and theory. , 2010, Journal of the American Chemical Society.

[47]  Lei Jiao,et al.  Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-yne/ene-vinylcyclopropanes and CO: homologous Pauson-Khand reaction and total synthesis of (+/-)-alpha-agarofuran. , 2010, Organic letters.

[48]  Zhi‐Xiang Yu,et al.  Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition reactions of 1-ene-, 1-yne- and 1-allene-vinylcyclopropanes. , 2010, Chemical communications.

[49]  M. Kerr,et al.  Heterocycles from cyclopropanes: applications in natural product synthesis. , 2009, Chemical Society reviews.

[50]  Donald G Truhlar,et al.  Performance of SM6, SM8, and SMD on the SAMPL1 test set for the prediction of small-molecule solvation free energies. , 2009, The journal of physical chemistry. B.

[51]  K N Houk,et al.  Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital models. , 2008, Journal of the American Chemical Society.

[52]  Siyu Ye,et al.  Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition of trans-vinylcyclopropane-enes. , 2008, Journal of the American Chemical Society.

[53]  K. Houk,et al.  Substituent effects, reactant preorganization, and ligand exchange control the reactivity in Rh(I)-catalyzed (5+2) cycloadditions between vinylcyclopropanes and alkynes. , 2008, Angewandte Chemie.

[54]  Zhi‐Xiang Yu,et al.  Tandem Rh(i)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin. , 2008, Journal of the American Chemical Society.

[55]  Claude Y. Legault,et al.  Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 + 2) cycloaddition reactions with vinylcyclopropanes. , 2008, Journal of the American Chemical Society.

[56]  Claude Y. Legault,et al.  Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles. , 2007, Journal of the American Chemical Society.

[57]  K N Houk,et al.  Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity. , 2007, Journal of the American Chemical Society.

[58]  V. Gevorgyan,et al.  Transition metal chemistry of cyclopropenes and cyclopropanes. , 2007, Chemical reviews.

[59]  C. Jun Transition metal-catalyzed carbon-carbon bond activation. , 2004, Chemical Society reviews.

[60]  K. Houk,et al.  On the mechanism of [Rh(CO)2Cl]2-catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes. , 2004, Journal of the American Chemical Society.

[61]  M. Frisch,et al.  Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields , 1994 .

[62]  M. Murakami,et al.  Selective activation of carbon–carbon bonds next to a carbonyl group , 1994, Nature.

[63]  Gernot Frenking,et al.  A set of f-polarization functions for pseudo-potential basis sets of the transition metals ScCu, YAg and LaAu , 1993 .

[64]  A. Becke Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[65]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[66]  P. Fuentealba,et al.  Pseudopotential calculations on Rb+2, Cs+2, RbH+, CsH+ and the mixed alkali dimer ions , 1982 .

[67]  Hermann Stoll,et al.  A proper account of core-polarization with pseudopotentials: single valence-electron alkali compounds , 1982 .

[68]  K. Fukui The path of chemical reactions - the IRC approach , 1981 .

[69]  P. C. Hariharan,et al.  The influence of polarization functions on molecular orbital hydrogenation energies , 1973 .

[70]  K. Fukui Formulation of the reaction coordinate , 1970 .

[71]  M. Murakami,et al.  Cleavage of Carbon—Carbon Single Bonds by Transition Metals , 1999 .

[72]  W. R. Wadt,et al.  Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals , 1985 .

[73]  W. R. Wadt,et al.  Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi , 1985 .