Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and 1H NMR experiment and DFT calculations

Journal of Molecular Structure

Volumn 987, Issue 1-3, 2011, Pages 166-173

  Fu, Gang ^a   Doerksen, Robert J ^a,b   Xu, Ping ^c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

1H NMR; Absolute configuration; Density functional theory; Diastereomer; Optical rotation; Sulfinyl dilactones

Indexed keywords

1H NMR; AB INITIO CALCULATIONS; ABSOLUTE CONFIGURATION; ASSIGNMENT OF ABSOLUTE CONFIGURATION; DFT CALCULATION; DIASTEREOMERS; EXPERIMENTAL TECHNIQUES; FIVE-MEMBERED RINGS; FLEXIBLE MOLECULES; H NMR SPECTRA; PROTEASOME INHIBITORS; SPECTROSCOPIC FEATURES; STEREOGENIC CENTERS; SULFINYL DILACTONES; THEORETICAL CALCULATIONS;

CALCULATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; ROTATION; STEREOCHEMISTRY;

DENSITY FUNCTIONAL THEORY;

EID: 79551506151     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.11.076     Document Type: Article

References (36)

1. J.G. Delcros, M.B. Floc'h, C. Prigent, and Y. Arlot-Bonnemains Curr. Med. Chem. 10 2003 479
2. A.F. Kisselev, and A.L. Goldberg Chem. Biol. 8 2001 739
3. G. Fu, X. Zou, Y. Fu, K. Mou, C. Ma, Y. Lu, and P. Xu J. Chin. Pharm. Sci. 16 2007 119
4. R. Bentley Chem. Soc. Rev. 34 2005 609
5. S. Allenmark, and J. Oxelbark Chirality 9 1997 638
6. H. Marom, P.U. Biedermann, and I. Agranat Chirality 19 2007 559
7. E.N. Suslova, I.A. Ushakov, and B.A. Shainyan Russ. J. General Chem. 77 2007 253
8. F. Yuste, B. Ortiz, J.I. Perez, A. Rodriguez-Hernandez, R. Sanchez-Obregon, F. Walls, and J.L.G. Ruano Tetrahedron 58 2002 2613
9. T.D. Crawford Theor. Chem. Acc. 115 2006 227
10. T.D. Crawford, M.C. Tam, and M.L. Abrams J. Phys. Chem. A 111 2007 12057
11. C. Bertucci, L.F.L. Guimaraes, P.S. Bonato, K.B. Borges, L.T. Okano, G. Mazzeo, and C. Rosini J. Pharm. Biomed. Anal. 52 2010 796
12. G. Mazzeo, E. Giorgio, R. Zanasi, N. Berova, and C. Rosini J. Org. Chem. 75 2010 4600
13. R. Mohammed, J.N. Peng, M. Kelly, M. Yousaf, E. Winn, S. Odde, Z. Bie, A.H. Xie, R.J. Doerksen, and M.T. Hamann Aust. J. Chem. 63 2010 877
14. P.L. Polavarapu Chem. Rec. 7 2007 125
15. E. Kleinpeter, A. Koch, and P.R. Seidl J. Phys. Chem. A 112 2008 4989 4995
16. G. Toth, J. Kovacs, A. Levai, E. Kleinpeter, and A. Koch Magn. Reson. Chem. 39 2001 251
17. E. Kleinpeter, S. Klod, and W.-D. Rudorf J. Org. Chem. 69 2004 4317
18. E. Kleinpeter, A. Schulenbrug, I. Zug, and H. Hartmann J. Org. Chem. 70 2005 6592
19. X.L. Sun, and Y.L. Wu Acta Chim. Sin. 55 1997 600
20. SYBYL 8.0, Tripos Associates, St. Louis, MO.
21. T.A. Halgren J. Comp. Chem. 17 1996 490
22. T.A. Halgren J. Comp. Chem. 20 1999 730
23. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
24. A.D. Becke J. Chem. Phys. 98 1993 5648
25. W.J. Hehre, and W.A. Lathan J. Chem. Phys. 56 1972 5255
26. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T.V. Jr., K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03. Revision D.01, Gaussian, Inc., Wallingford CT, 2004.
27. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, and M.J. Frisch J. Phys. Chem. A 105 2001 5356
28. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, M.J. Frisch, O. Bortolini, and P. Besse Chirality 15 2003 S57
29. J. Olsen, and P. Joergensen J. Chem. Phys. 82 1985 3235
30. J.R. Cheeseman, M.J. Frisch, F.J. Devlin, and P.J. Stephens J. Phys. Chem. A 104 2000 1039
31. B. Mennucci, J. Tomasi, R. Cammi, J.R. Cheeseman, M.J. Frisch, F.J. Devlin, S. Gabriel, and P.J. Stephens J. Phys. Chem. A 106 2002 6102
32. D. Marchesan, S. Coriani, C. Forzato, P. Nitti, G. Pitacco, and K. Ruud J. Phys. Chem. A 109 2005 1449
33. S. Coriani, A. Baranowska, L. Ferrighi, C. Forzato, D. Marchesan, P. Nitti, G. Pitacco, A. Rizzo, and K. Ruud Chirality 18 2006 357
34. K. Wolinski, J.F. Hinton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251
35. P.R. Rablen, S.A. Pearlman, and J. Finkbiner J. Phys. Chem. A 103 1999 7357
36. R. Jain, T. Bally, and P.R. Rablen J. Org. Chem. 74 2009 4017