Challenges in the assignment of relative and absolute configurations of complex molecules: Computation can resolve conflicts between theory and experiment

Tetrahedron

Volumn 69, Issue 48, 2013, Pages 10351-10356

  Ren, Jie ^a   Li, Guo You ^b   Shen, Lan ^a   Zhang, Guo Lin ^b   Nafie, Laurance A ^c   Zhu, Hua Jie ^a  

^a HEBEI UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c SYRACUSE UNIVERSITY   (United States)

Author keywords

Absolute configuration reassignment; Chiroptical spectroscopy; DFT; Transition state; X ray

Indexed keywords

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CHIRALITY; DENSITY FUNCTIONAL THEORY; ENERGY CONVERSION; EXPERIMENT; HYDROLYSIS; MOLECULE; PRIORITY JOURNAL; X RAY ANALYSIS;

EID: 84887124184     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.10.004     Document Type: Article

References (29)

1. G.-Y. Li, T. Yang, Y.-G. Luo, X.-Z. Chen, D.-M. Fang, and G.-L. Zhang Org. Lett. 11 2009 3714 3717
2. L. Shen, S.-D. Zhao, and H.-J. Zhu Chem. J. Chin. Univ. 32 2011 2568 2573
3. Q.-M. Li, J. Ren, L. Shen, B. Bai, X.-C. Liu, M.-L. Wen, and H.-J. Zhu Tetrahedron 69 2013 3067 3074
4. S.D. Zhao, L. Shen, D.Q. Luo, and H.J. Zhu Curr. Org. Chem. 15 2011 1843 1862
5. H.J. Zhu Modern Organic Stereochemistry 2009 Science Beijing, China
6. P.L. Polavarapu Mol. Phys. 91 1997 551 554
7. A. de Meijere, A.F. Khlebnikov, S.I. Kozhushkov, R.R. Kostikov, P.R. Schreiner, A. Wittkopp, C. Rinderspacher, H. Menzel, D.S. Yufit, and J.A.K. Howard Chem. - Eur. J. 8 2002 828 842
8. T. Taniguchi, C. Martin, K. Monde, K. Nakanishi, N. Berova, and L. Overman J. Nat. Prod. 72 2009 430 432
9. D.M. McCann, and P.J. Stephens J. Org. Chem. 71 2006 6074 6098
10. B. Mennucci, M. Claps, A. Evidente, and C. Rosini J. Org. Chem. 72 2007 6680 6691
11. M. Cheng, Q. Li, B. Lin, Y. Sha, J. Ren, Y. He, Q. Wang, H. Hua, and K. Ruud Tetrahedron: Asymmetry 17 2006 179 183
12. T.-G. Liao, J. Ren, H.-F. Fan, M.-J. Xie, and H.-J. Zhu Tetrahedron: Asymmetry 19 2008 808 815
13. P.J. Stephens, J.J. Pan, F.J. Devlin, K. Krohn, and T. Kurtan J. Org. Chem. 72 2007 3521 3536
14. X.-N. Li, Y. Zhang, X.-H. Cai, T. Feng, Y.-P. Liu, Y. Li, J. Ren, H.-J. Zhu, and X.-D. Luo Org. Lett. 13 2011 5896 5899
15. Z.Y. Lu, H.J. Zhu, P. Fu, Y. Wang, Z.H. Zhang, H.P. Lin, P.P. Liu, Y.B. Zhuang, K. Hong, and W.M. Zhu J. Nat. Prod. 73 2010 911 914
16. Y.L. Zhang, H.M. Ge, W. Zhao, H. Dong, Q. Xu, S.H. Li, J. Li, J. Zhang, Y.C. Song, and R.X. Tan Angew. Chem., Int. Ed. 47 2008 5823 5826
17. E. Giorgio, N. Parrinello, S. Caccamese, and C. Rosini Org. Biomol. Chem. 2 2004 3602 3607
18. K.M. Specht, J. Nam, D.M. Ho, N. Berova, R.K. Kondru, D.N. Beratan, P. Wipf, R.A. Pittman Jr., and D. Kahne J. Am. Chem. Soc. 123 2001 8961 8966
19. W.L. Xiao, C. Lei, J. Ren, T.-G. Liao, J.-X. Pu, C.U. Pittman, Y. Lu, Y.-T. Zheng, H.-J. Zhu, and H.-D. Sun Chem. - Eur. J. 14 2008 11584 11592
20. L.-C. Li, J. Ren, J.-X. Jiang, and H.-J. Zhu Eur. J. Org. Chem. 2007 1026 1030
21. L.A. Nafie Nat. Prod. Commun. 3 2008 451 466
22. A. Nakahashi, Y. Yaguchi, N. Miura, M. Emura, and K. Monde J. Nat. Prod. 74 2011 707 711
23. F. Wang, P.L. Polavarapu, F. Lebon, G. Longhi, S. Abbate, and M. Catellani J. Phys. Chem. A 106 2002 12365 12369
24. C. Socolsky, S.M.K. Rates, A.C. Stein, Y. Asakawa, and A. Bardon J. Nat. Prod. 75 2012 1007 1017
25. T. Taniguchi, and K. Monde J. Am. Chem. Soc. 134 2012 3695 3698
26. V.P. Nicu, E.J. Baerends, and P.L. Polavarapu J. Phys. Chem. A 116 2012 8366 8373
27. Y. He, B. Wang, R.K. Dukor, and L.A. Nafie Appl. Spectrosc. 70 2011 699 723
28. G. Zuber, and W. Hug J. Phys. Chem. A 108 2004 2108 2118
29. Y. Zou, D. Garayalde, Q. Wang, C. Nevado, and A. Goeke Angew. Chem., Int. Ed. 47 2008 10110 10113