1,2-Disubstituted Planar Chiral Ferrocene Derivatives from Sulfonamide-Directed ortho-Lithiation: Synthesis, Absolute Configuration, and Chiroptical Properties

A straightforward approach to the synthesis of a series of 1,2-disubstituted planar chiral ferrocenes was achieved using the ortho-directed lithiation of chiral ferrocenesulfonamides followed by a ...

[1]  V. Barone,et al.  Unbiased Determination of Absolute Configurations by Vis-à-Vis Comparison of Experimental and Simulated Spectra: The Paradigmatic Case of Diplopyrone. , 2019, The journal of physical chemistry. B.

[2]  V. Barone,et al.  Two-level stochastic search of low-energy conformers for molecular spectroscopy: implementation and validation of MM and QM models. , 2019, Physical chemistry chemical physics : PCCP.

[3]  V. Barone,et al.  Ferrocenes with simple chiral substituents: an in-depth theoretical and experimental VCD and ECD study. , 2019, Physical chemistry chemical physics : PCCP.

[4]  V. Dimitrov,et al.  Directed ortho-lithiation as a tool for synthesis of chiral 1,2-disubstituted arylsulfonamides , 2018, Monatshefte für Chemie - Chemical Monthly.

[5]  G. Pescitelli,et al.  Synthesis and structure analysis of ferrocene‐containing pseudopeptides , 2018, Biopolymers.

[6]  A. Cimmino,et al.  Importance and Difficulties in the Use of Chiroptical Methods to Assign the Absolute Configuration of Natural Products: The Case of Phytotoxic Pyrones and Furanones Produced by Diplodia corticola. , 2017, Journal of natural products.

[7]  J. Okuda Ferrocene – 65 Years After , 2017 .

[8]  V. Barone The virtual multifrequency spectrometer: a new paradigm for spectroscopy , 2016, Wiley interdisciplinary reviews. Computational molecular science.

[9]  Stuart Cantrill,et al.  Wrong but seminal. , 2016, Nature chemistry.

[10]  Marco Fusè,et al.  VCD spectroscopy as an excellent probe of chiral metal complexes containing a carbon monoxide vibrational chromophore. , 2015, Chemical communications.

[11]  G. Sheldrick Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[12]  A. Mándi,et al.  On the complementarity of ECD and VCD techniques. , 2014, Chirality.

[13]  V. Barone,et al.  High-Accuracy Vibrational Computations for Transition-Metal Complexes Including Anharmonic Corrections: Ferrocene, Ruthenocene, and Osmocene as Test Cases. , 2014, Journal of chemical theory and computation.

[14]  M. Stoyanova,et al.  Palladium‐Catalyzed Allylic Alkylation Using Chiral P,O‐Ligands Synthesized via Sulfonamide Directed ortho‐Lithiation. , 2014 .

[15]  Saeed Amirjalayer,et al.  Amplified vibrational circular dichroism as a probe of local biomolecular structure. , 2014, Journal of the American Chemical Society.

[16]  Heinz-Bernhard Kraatz,et al.  Stimuli-responsive supramolecular gelation in ferrocene-peptide conjugates. , 2013, Chemistry.

[17]  H. Lang,et al.  Selective Syntheses of Planar-Chiral Ferrocenes , 2013 .

[18]  Louis J. Farrugia,et al.  WinGX and ORTEP for Windows: an update , 2012 .

[19]  P. Stephens,et al.  VCD Spectroscopy for Organic Chemists , 2012 .

[20]  F. Lipparini,et al.  Toward Ab Initio Anharmonic Vibrational Circular Dichroism Spectra in the Condensed Phase. , 2012, The journal of physical chemistry letters.

[21]  H. Werner At least 60 years of ferrocene: the discovery and rediscovery of the sandwich complexes. , 2012, Angewandte Chemie.

[22]  Laurence A. Nafie,et al.  Vibrational Optical Activity: Principles and Applications , 2011 .

[23]  Edward K. Hawkins,et al.  A single chiroptical spectroscopic method may not be able to establish the absolute configurations of diastereomers: dimethylesters of hibiscus and garcinia acids. , 2011, The journal of physical chemistry. A.

[24]  B. Ivanova,et al.  Highly diastereoselective ortho-lithiation of chiral ferrocenecarboxamides , 2010 .

[25]  C. Macrae,et al.  Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures , 2008 .

[26]  V. Sokolov,et al.  Circular dichroism of optically active planar chiral cyclopalladium ferrocene derivatives. Investigation of the dimer-monomer equilibrium , 2007 .

[27]  A. Moscowitz Theoretical Aspects of Optical Activity Part One: Small Molecules , 2007 .

[28]  Javier Adrio,et al.  Recent applications of chiral ferrocene ligands in asymmetric catalysis. , 2006, Angewandte Chemie.

[29]  S. Ogawa,et al.  Synthesis of New Pentathiepin and Dithiatriselenepin Fused to Ferrocene via Dithiametallacycles , 2005 .

[30]  F. Weigend,et al.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. , 2005, Physical chemistry chemical physics : PCCP.

[31]  S. Ogawa,et al.  Synthesis, structure, and electrochemical properties of biferrocenes annulated with 1,2-dithiin and 1,2-dithiin 1,1-dioxides , 2005 .

[32]  S. Ogawa,et al.  First synthesis and structure of sulfur-containing heterocycles fused to ferrocene , 2002 .

[33]  O. Familoni Metalated Sulfonamides and Their Synthetic Applications , 2002 .

[34]  A. Burchat,et al.  Titration of alkyllithiums with a simple reagent to a blue endpoint , 1997 .

[35]  Wang,et al.  Accurate and simple analytic representation of the electron-gas correlation energy. , 1992, Physical review. B, Condensed matter.

[36]  F. Allen,et al.  The crystallographic information file (CIF) : a new standard archive file for crystallography , 1991 .

[37]  J. Autschbach Computing chiroptical properties with first-principles theoretical methods: background and illustrative examples. , 2009, Chirality.

[38]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[39]  Ana G. Petrovic,et al.  Kramers-Kronig transformation of experimental electronic circular dichroism: application to the analysis of optical rotatory dispersion in dimethyl-L-tartrate. , 2006, Chirality.

[40]  H. Falk,et al.  Stereochemie von metallocenen, 29. Mitt , 1969 .