Stereodynamics and absolute configuration of stereolabile atropisomers in 2,2-dimethyl-1-aryl-1-indanols

Chirality

Volumn 23, Issue 9, 2011, Pages 768-778

  Casarini, Daniele ^a   Mancinelli, Michele ^b   Mazzanti, Andrea ^b   Boschi, Francesca ^b,c  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c COMECER SpA ^*  (Italy)

Author keywords

DFT calculations; dynamic NMR; electronic circular dichroism; enantioselective HPLC; indanols

Indexed keywords

INDAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; MOLECULAR DYNAMICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; X RAY DIFFRACTION;

EID: 80052812598     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20988     Document Type: Article

References (47)

1. Casarini D, Lunazzi L, Mazzanti A, Foresti E,. Conformational studies by dynamic NMR. 64. Stereomutations of atropisomers and of conformational enantiomers in ethers of hindered naphthylcarbinols. J Org Chem 1998; 63: 4746-4754. (Pubitemid 128501312)
2. Casarini D, Coluccini C, Lunazzi L, Mazzanti A,. Stereolabile and configurationally stable atropisomers of hindered aryl carbinols. J Org Chem 2005; 70: 5098-5102. (Pubitemid 40863911)
3. Casarini D, Lunazzi L, Mazzanti A, Mancinelli M,. Conformation and stereodynamics of symmetrically ortho-disubstituted aryl carbinols and aryl ethers. J Org Chem 2007; 72: 998-1004. (Pubitemid 46233372)
4. Casarini D, Lunazzi L, Mazzanti A, Mancinelli M,. Structure, conformations, stereodynamics, dimer formation and absolute configuration of axially chiral atropisomers of hindered biphenyl carbinols. J Org Chem 2007; 72: 7667-7676. (Pubitemid 47501635)
5. Cheer JC, Johonson CR,. The stereoselective rearrangements of conformationally mobile epoxides. J Am Chem Soc 1968; 90: 178-183.
6. Palmer M, Walsgrove T, Wills M,. (1R,2S)-(+)-cis-1-Amino-2-indanol: an effective ligand for asymmetric catalysis of transfer hydrogenations of ketones. J Org Chem 1997; 62: 5226-5228. (Pubitemid 27328185)
7. Brewster JH, Buta JG,. Conformational mobility and optical rotation effects of aromatic nuclei. J Am Chem Soc 1966; 88: 2233-2240.
8. Al-Saadi AA, Wagner M, Laane J,. Spectroscopic and computational studies of the intramolecular hydrogen bonding of 2-indanol. J Phys Chem A 2006; 110: 12292-12297. (Pubitemid 44806874)
9. Pincock JA, Wedge PJ,. The photochemistry of conformationally rigid benzilic esters:2,2-dimethyl-1-indanyl acetates and pivalates. J Org Chem 1995; 60: 4067-4076.
10. Orliac-le Moing A, Delauny J, LeBouc A, Simonet J,. Reduction electrochimique des derives carbonyles insatures. IX. Indanones et tetralones: electrolyses mixtes en presence d'electrophiles. Tetrahedron 1985; 41: 4483-4493.
11. Fuson RC, Corse J, Welldon PB,. Enediols. VIII. Methoxystilbenediols J Org Chem 1941; 63: 2645-2648.
12. Bradley SA, Krishnamurthy K,. A modified CRISIS-HSQC for band-selective IMPRESS. Magn Res Chem 2005; 43: 117-123. (Pubitemid 40814518)
13. Willker W, Leibfritz D, Kerssebaum R, Bermel W,. Gradient selection in inverse heteronuclear correlation spectroscopy. Magn Res Chem 1993; 31: 287-292.
14. Hurd RE, John BK,. Gradient-enhanced proton-detected heteronuclear multiple-quantum coherence spectroscopy. J Magn Reson 1991; 91: 648-653.
15. Stott K, Stonehouse J, Keeler J, Hwand TL, Shaka AJ,. Excitation sculpting in high-resolution nuclear magnetic resonance spectroscopy: Application to selective NOE experiments. J Am Chem Soc 1995; 117: 4199-4200.
16. Kupče E, Boyd J, Campbell ID,. Short selective pulses for biochemical applications. J Magn Reson Series B 1995; 106: 300-303.
17. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas, O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA,. Gaussian 03, Revision D.01. Wallingford CT: Gaussian, Inc.; 2005.
18. Frisch M J, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M,., Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ,. Gaussian 09, Revision A.1. Wallingford, CT: Gaussian, Inc., 2009.
19. Ayala PY, Schlegel HB,. Identification and treatment of internal rotation in normal mode vibrational analysis. J Chem Phys 1998; 108: 2314-2325. (Pubitemid 128604692)
20. Casarini D, Lunazzi L, Mazzanti A,. Recent advances in stereodynamics and conformational analysis by dynamic NMR spectroscopy and theoretical calculations. Eur J Org Chem 2010; 2035-2056.
21. Donnington RD, Keith TA, Millam JM,. Gaussview 5.0.9. Semichem, 2008.
22. Lomas JS, Luong PK, Dubois JE,. Nucleophilic addition of o-tolyllithium compounds to di-tert-butyl ketone. Thermal and organolithium-catalyzed isomerization of o-tolyldi-tert-butylcarbinol rotamers. J Org Chem 1977; 42: 3394-3399.
23. 3 rotation of anti-o-tolyldi(1-adamantyl)methane. J Org Chem 1995; 60: 3246-3248.
24. Jennings WB,. Chemical shift nonequivalence in prochiral groups. Chem Rev 1975; 75: 307-322.
25. Casarini D, Lunazzi L, Mazzanti A,. Correlated rotations in benzylfluorene derivatives: structure, conformation and stereodynamics. J Org Chem 2007; 73: 2811-2818. (Pubitemid 351482993)
26. Casarini D, Lunazzi L, Mazzanti A,. Steric effects which determine the conformational preferences and stereodynamic processes of aryl fluorenyl ketones. Org. Biomol Chem 2009; 7: 1619-1626.
27. Grilli S, Lunazzi L, Mazzanti A, Casarini D, Femoni C,. Conformational studies by dynamic NMR. 78. Stereomutation of the helical enantiomers of trigonal carbon diaryl-substituted compounds: dimesitylketone, -thioketone and -ethylene. J Org Chem 2001; 66: 488-495. (Pubitemid 32105566)
28. Mislow K,. Stereochemical consequences of correlated rotation in molecular propellers. Acc Chem Res 1976; 9: 26-33.
29. Mazzanti A, Lunazzi L, Ruzziconi R, Spizzichino S, Schlosser M,. The torsional barriers of 2-hydroxy- and 2-fluorobiphenyl: small, but measurable. Chem Eur J 2010; 16: 9186-9192.
30. Anet FAL, Chmurni GN, Krane J,. Ring inversion in cyclohexanone. J Am Chem Soc 1973; 95: 4423-4424.
31. Pawar DM, Miggins SD, Smith SV, Noe EA,. Conformational study of cis-cyclononene by dynamic NMR spectroscopy and computational methods. J Org Chem 1999; 64: 2418-2421. (Pubitemid 29180461)
32. Casarini D, Grilli S, Lunazzi L, Mazzanti A,. Conformational studies by dynamic NMR. 80. Cog-Wheel effect in the stereolabile helical enantiomers of dimesityl sulfoxide and sulfone. J Org Chem 2001; 66: 2757-2763. (Pubitemid 32867695)
33. Bringmann G, Bruhn T, Maksimenka K, Hemberger Y,. The assignment of absolute stereostructures through quantum chemical circular dichroism calculations. Eur J Org Chem 2009: 2717-2727.
34. Stephens PJ, Pan JJ, Devlin FJ, Krohn K, Kurtán K,. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: The iridoids plumericin and isoplumericin. J Org Chem 2007; 72: 3521-3536. (Pubitemid 46668155)
35. Kwit M, Rozwadowska MD, Gawroński J, Grajewska A,. Density functional theory calculations of the optical rotation and electronic circular dichroism: The absolute configuration of the highly flexible trans-isocytoxazone revised. J Org Chem 2009; 74: 8051-8063.
36. Gioia C, Fini F, Mazzanti A, Bernardi L, Ricci A,. Organocatalytic asymmetric formal [3 + 2] cycloaddition with in situ-generated N-carbamoyl nitrones J Am Chem Soc 2009; 131: 9614-9615.
37. Pescitelli G, Di Pietro S, Cardellicchio C, Annunziata M, Capozzi M, Di Bari L,. Systematic investigation of CD spectra of aryl benzyl sulfoxides interpreted by means of TDDFT calculations. J Org Chem 2010; 75: 1143-1154.
38. Bencivenni G, Wu L-Y, Giannichi B, Mazzanti A, Pesciaioli F, Song M-P, Bartoli G, Melchiorre P,. Targeting structural and stereochemical complexity by asymmetric organocascade: construction of spirocyclic oxindoles having multiple stereocenters. Angew Chem Int Ed Engl 2009; 48: 7200-7203.
39. Yanai T, Tew D, Handy N,. A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 2004; 393: 51-57.
40. 2](1,4) barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J Am Chem Soc 2004; 126: 7514-7521. (Pubitemid 38781485)
41. D'Acquarica I, Gasparrini F, Pierini M, Villani C, Zappia G,. Dynamic HPLC on chiral stationary phases: a powerful tool for the investigation of stereomutation processes. J Sep Sci 2006; 29: 1508-1516. (Pubitemid 44122018)
42. Trapp O,. unified equation for access to rate constants of first-order reactions in dynamic and on-column reaction chromatography. Anal Chem 2006; 78: 189-198. (Pubitemid 43050154)
43. Wolf C,. Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods. Chem Soc Rev 2005; 34: 595-608. (Pubitemid 40992747)
44. Trapp O, Shellie R, Marriott P, Schurig V,. Simulation of elution profiles for two-dimensional dynamic gas chromatographic experiments. Anal Chem 2003; 75: 4452-4461. (Pubitemid 37082234)
45. Trapp O, Schurig V,. Stereointegrity of Tröger's base: gas-chromatographic determination of the enantiomerization barrier. J Am Chem Soc 2000; 122: 1424-1430. (Pubitemid 30120426)
46. Alcaro S, Casarini D, Gasparrini F, Lunazzi L, Villani C,. Atropisomerism in hindered naphthyl sulfones investigated by dynamic NMR and dynamic HPLC techniques. J Org Chem 1995; 60: 5515-5519.
47. Casarini D, Lunazzi L, Mazzanti A,. Conformational studies by dynamic nuclear magnetic resonance. Part 59. Stereodynamics of conformational enantiomers in the atropisomers of hindered naphthilcarbinols. J Org Chem 1997; 62: 3315-3323.