A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid

Journal of Molecular Modeling

Volumn 20, Issue 8, 2014, Pages

  Tognetti, Vincent ^a   Boulangé, Agathe ^a   Peixoto, Philippe A ^a   Franck, Xavier ^a   Joubert, Laurent ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Bader's atoms in molecules theory; Density functional theory; Dual descriptor; Hypervalent iodine; Hypervalent twist; Oxidative dearomatization

Indexed keywords

BENZOIC ACID DERIVATIVE; IODOXYBENZOIC ACID; PROTEIN; SOLVENT; UNCLASSIFIED DRUG; 2-IODOXYBENZOIC ACID; AROMATIC HYDROCARBON; BENZOPYRAN DERIVATIVE; CATION; EPICOCCONONE; FURAN DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; KETONE;

AROMATIZATION; ARTICLE; CONCEPTUAL FRAMEWORK; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; ORGANIC CHEMISTRY; OXIDATION; OXIDATIVE DEAROMATIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SOLVENT EFFECT; STEREOCHEMISTRY; THEORETICAL STUDY; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; THEORETICAL MODEL; THERMODYNAMICS;

BENZOPYRANS; CATIONS; FURANS; HYDROCARBONS, AROMATIC; IODOBENZOATES; KETONES; MODELS, THEORETICAL; OXIDATION-REDUCTION; STEREOISOMERISM; THERMODYNAMICS;

EID: 84904276332     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-014-2342-1     Document Type: Article

References (59)

1. Wirth T (ed) (2003) Hypervalent iodine chemistry. Springer, Berlin
2. Zhdankin VV (2009) Hypervalent iodine(III) reagents in organic synthesis. Arkivoc (i) 1-62
3. Ladziata U, Zhdankin VV (2006) Hypervalent iodine(V) reagents in organic synthesis. ARKIVOC (ix) 26-58 (Pubitemid 43184437)
4. Silva LF Jr, Olofssonb B (2011) Hypervalent iodine reagents in the total synthesis of natural products. Nat Prod Rep 28:1722-1754
5. Yusubov MS, Zhdankin VV (2012) Hypervalent iodine reagents and green chemistry. Curr Org Synth 9:247-272
6. Liang H, Ciufolini MA (2011) Chiral hypervalent iodine reagents in asymmetric reactions. Angew Chem Int Ed 50:11849-11851
7. Shah AA, Khan ZA, Choudhary N et al (2009) Iodoxolone-based hypervalent iodine reagents. Org Lett 11:3578-3581
8. 3-iodinane compounds. J Org Chem 78:11096-11101
9. Yoshimura A, Middleton KR, Todora AD et al (2013) Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes. Org Lett 15: 4010-4013
10. Satam V, Harad A, Rajule R et al (2010) 2-Iodoxybenzoic acid (IBX): an efficient hypervalent iodine reagent. Tetrahedron 66:7659-7706
11. Frigerio M, Santagostino M (1994) A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO. Tetrahedron Lett 35:8019-8022 (Pubitemid 24320215)
12. Zhdankin VV, Stang PJ (2002) Recent developments in the chemistry of polyvalent iodine compounds. Chem Rev 102:2523-2584 (Pubitemid 35377635)
13. Nicolaou KC, Baran PS, Zhong Y-L (2001) Selective oxidation at carbon adjacent to aromatic systems with IBX. J Am Chem Soc 123: 3183-3185 (Pubitemid 32879605)
14. Stang PJ (2003) Polyvalent iodine in organic chemistry. J Org Chem 68:2997-3008
15. Stang PJ, Zhdankin VV (2008) Chemistry of polyvalent iodine. Chem Rev 108:5299-5358
16. Uyanik M, Ishihara K (2009) Hypervalent iodine-mediated oxidation of alcohols. Chem Commun 2086-2099
17. Uyanik M, Akakura M, Ishihara K (2009) 2-Iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone. J Am Chem Soc 131:251-262
18. Kommreddy A, Bowsher MS, Gunna MR et al (2008) Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative. Tetrahedron Lett 49:4378-4382
19. Thottumkara AP, Thottumkara KV (2002) Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent. Tetrahedron Lett 43:569-572 (Pubitemid 34085015)
20. Quideau S, Pouységu L, Deffieux D (2008) Oxidative dearomatization of phenols: why, how and what for? Synlett 4:467-495 (Pubitemid 351412774)
21. Pouységu L, Sylla T, Garnier T et al (2010) Hypervalent iodinemediated oxygenative phenol dearomatization reactions. Tetrahedron 66:5908-5917
22. Uyanik M, Yasui T, Ishihara K (2013) Hydrogen bonding and alcohol effects in asymmetric hypervalent iodine catalysis: enantioselective oxidative dearomatization of phenols. Angew Chem Int Ed 52: 9215-9218
23. Boulangé A, Peixoto PA, Franck X (2011) Diastereoselective IBX oxidative dearomatization of phenols by remote induction: towards the epicocconone core framework. Chem-Eur J 17:10241-10245
24. Bell PJL, Karuso P (2003) Epicocconone, a novel fluorescent compound from the fungus Epicoccum nigrum. J Am Chem Soc 125: 9304-9305 (Pubitemid 36936045)
25. Coghlan DR, Mackintosh JA, Karuso P (2005) Mechanism of reversible fluorescent staining of protein with epicocconone. Org Lett 7:2401-2404 (Pubitemid 40847646)
26. Choi HY, Veal DA, Karuso P (2006) Epicocconone, a new cell-permeable long Stokes' shift fluorescent stain for live cell imaging and multiplexing. J Fluoresc 16:475-482 (Pubitemid 44048522)
27. Mackintosh JA, Choi HY, Bae SH et al (2003) A fluorescent natural product for ultra sensitive detection of proteins in 1-D and 2-D gel electrophoresis. Proteomics 3:2273-2288 (Pubitemid 38010105)
28. Panda D, Datta A (2007) Evidence for covalent binding of epicocconone with proteins from synchronous fluorescence spectra and fluorescence lifetimes. J Chem Sci 119:99-104 (Pubitemid 46715191)
29. Chevalier F (2010) Standard dyes for total protein staining in gel-based proteomic analysis. Materials 3:4784-4792
30. Smejkal GB, Robinson MH, Lazarev A (2004) Comparison of fluorescent stains: relative photostability and differential staining of proteins in two-dimensional gels. Electrophoresis 25:2511-2519 (Pubitemid 39193660)
31. Peixoto P (2009) Synthesis of new fluorescent biomarkers based on the structure of epicocconone for the detection of proteins. Ph.D. thesis. Université de Rouen, Mont-Saint-Aignan
32. Boulangé A (2012) Synthesis of analogues of epicocconone by oxidative dearomatization reaction. Structure-fluorescence relationship and proteomics applications. Ph.D. thesis. Université de Rouen, Mont-Saint-Aignan
33. Syzgantseva OA, Tognetti V, Joubert L et al (2012) Electronic excitations in epicocconone analogues: TDDFT methodological assessment guided by experiment. J Phys Chem A 116:8634-8643
34. Chatterjee S, Karuso P, Boulangé A et al (2013) The role of different structural motifs in the ultrafast dynamics of second generation protein stains. J Phys Chem B 117:14951-14959
35. Syzgantseva OA, Tognetti V, Boulangé A et al (2014) Evaluating charge transfer in epicocconone analogues: towards a targeted design of fluorophores. J Phys Chem A 118:757-764
36. Frisch MJ et al (2009) Gaussian 09, revision B.01. Gaussian, Inc., Wallingford
37. Lynch BJ, Fast PL, Harris M et al (2000) Adiabatic connection for kinetics. J Phys Chem A 104:4811-4815
38. Su JT, Goddard WA III (2005) Enhancing 2-iodoxybenzoic acid reactivity by exploiting a hypervalent twist. J Am Chem Soc 127: 14146-14147 (Pubitemid 41457555)
39. Hay PJ, Wadt WR (1985) Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg. J Chem Phys 82:270-283
40. Check CE, Faust TO, Bailey JM et al (2001) Addition of polarization and diffuse functions to the LANL2DZ basis set for P-block elements. J Phys Chem A 105:8111-8116 (Pubitemid 35373232)
41. Fukui K (1981) The path of chemical reactions-the IRC approach. Acc Chem Res 14:363-368
42. Gonzalez C, Schlegel HB (1990) Reaction path following in massweighted internal coordinates. J Phys Chem 94:5523-5527
43. Cancès E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anistropic dielectrics. J Chem Phys 107:3032-41 (Pubitemid 127568923)
44. Scalmani G, Frisch MJ (2010) Continuous surface charge polarizable continuum models of solvation. I. General formalism. J Chem Phys 132:114110
45. Bader RFW (1990) Atoms in molecules: a quantum theory. Oxford University Press, Oxford
46. Keith TA (2012) AIMAll (version 12.09.23). TK Gristmill Software, Overland Park
47. Chermette H (1999) Chemical reactivity indexes in density functional theory. J Comput Chem 20:129-154
48. Geerlings P, De Proft F, Langenaeker W (2003) Conceptual density functional theory. Chem Rev 103:1793-1873
49. Morell C, Grand A, Toro-Labbé A (2005) A new dual descriptor for chemical reactivity. J Phys Chem A 109:205-212 (Pubitemid 40121037)
50. Zielinski F, Tognetti V, Joubert L (2012) Condensed descriptors for reactivity. A methodological study. Chem Phys Lett 527:67-72
51. Tognetti V, Morell C, Ayers PW et al (2013) A proposal for an extended dual descriptor: a possible solution when frontier molecular orbital theory fails. Phys Chem Chem Phys 15:14465-14475
52. Moorthy JN, Senapati K, Parida KN et al (2011) Twist does a twist to the reactivity: stoichiometric and catalytic oxidations with twisted tetramethyl-IBX. J Org Chem 76:9593-9601
53. Guilbault A-A, Legault CY (2012)Drastic enhancement of activity in iodane-based α-tosyloxylation of ketones: iodine(III) does the hypervalent twist. ACS Catal 2:219-222
54. Sajith PK, Suresh CH (2013) Trans and cis influences in hypervalent iodine(III) complexes: a DFT study. Inorg Chem 52:6046-6054
55. Fradera X, Austen MA, Bader RFW (1999) The Lewis model and beyond. J Phys Chem A 103:304-314 (Pubitemid 129589280)
56. Firme CL, Antunes OAC, Esteves PM (2007) Electronic nature of planar cyclobutenyl dication derivatives. J Phys Chem A 111:11904- 11907
57. Pinter B, Van Speybroeck V, Waroquier M et al (2013) Trans effect and trans influence: importance of metal mediated ligand- ligand repulsion. Phys Chem Chem Phys 15:17354- 17365
58. Popelier PLA (2012) Quantum chemical topology: knowledgeable atoms in peptides. AIP Conf Proc 1456:261-268
59. Stewart JPP (2007) Optimization of parameters for semi-empirical methods. V. Modification of NDDO approximations and application to 70 elements. J Mol Model 13:1173-1213