Synthesis and structure of stereoisomeric multivicinal hexafluoroalkanes

Angewandte Chemie - International Edition

Volumn 48, Issue 30, 2009, Pages 5457-5460

  Hunter, Luke ^a   Kirsch, Peer ^b   Slawin, Alexandra M Z ^a   O'Hagan, David ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b MERCK KGAA   (Germany)

Author keywords

Conformation analysis; Fluorine; Organofluorine chemistry; Stereochemistry

Indexed keywords

A-CARBON; C-F BONDS; CONFORMATION ANALYSIS; FLUORINE ATOMS; ORGANOFLUORINE CHEMISTRY; RATIONAL EXPECTATIONS; STEREOCHEMICAL EFFECTS; ZIGZAG SHAPE;

CONFORMATIONS; FLUORINE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

X RAY CRYSTALLOGRAPHY;

ALKANE; FLUORINATED HYDROCARBON; FLUORINE;

CHEMISTRY; CONFORMATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKANES; CRYSTALLOGRAPHY, X-RAY; FLUORINE; HYDROCARBONS, FLUORINATED; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 70349779000     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901956     Document Type: Article

References (30)

1. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
2. a) W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369
3. b) K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
4. a) J. A. Hodges, R. T. Raines, J. Am. Chem. Soc. 2005, 127, 15923-15932
5. b) R. I. Mathad, B. Jaun, O. Flögel, J. Gardiner, M. Löweneck, J. D. C. Codée, P. H. Seeberger, D. Seebach, M. K. Edmonds, F. H. M. Graichen, A. D. Abell, Helv. Chim. Acta 2007, 90, 2251-2273.
6. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319.
7. N. E. J. Gooseman, D. O'Hagan, M. J. G. Peach, A. M. Z. Slawin, D. T. Tozer, R. J. Young, Angew. Chem. 2007, 119, 6008-6012
8. Angew. Chem. Int. Ed. 2007, 46, 5904-5908.
9. L. Hunter,D. O'Hagan, Org. Biomol. Chem. 2008, 6, 2843-2848.
10. a) M. Schüler, D. O'Hagan, A. M. Z. Slawin, Chem. Commun. 2005, 4324-4326
11. b) M. Tavasli, D. O'Hagan, C. Pearson, M. C. Petty, Chem. Commun. 2002, 1226-1227.
12. a) M. Nicoletti, D. O'Hagan, A. M. Z. Slawin, J. Am. Chem. Soc. 2005, 127, 482-483
13. b) M. Nicoletti, M. Bremer, P. Kirsch, D. O'Hagan, Chem. Commun. 2007, 5075-5077.
14. a) L. Hunter, D. O'Hagan, A. M. Z. Slawin, J. Am. Chem. Soc. 2006, 128, 16422-16423
15. b) L. Hunter, P. Kirsch, J. T. G. Hamilton, D. O'Hagan, Org. Biomol. Chem. 2008, 6, 3105-3108.
16. L. Hunter, A. M. Z. Slawin, P. Kirsch, D. O'Hagan, Angew. Chem. 2007, 119, 8033-8036
17. Angew. Chem. Int. Ed. 2007, 46, 7887-7890.
18. D. Wu, A. Tian, H. Sun, J. Phys. Chem. A 1998, 102, 9901-9905.
19. A similar steric repulsion occurs if a C-F bond is aligned parallel to a C-C bond in the β position.
20. L. Goodman, H. Gu, V. Pophristic, J. Phys. Chem. A 2005, 109, 1223-1229.
21. M. E. Neubert, S. A. Keast, J. M. Kim, K. J. Miller, R. M. Murray, A. G. Norton, R. A. Shenoy, M. E. Walsh, R. G. Petschek, Liq. Cryst. 2004, 31, 175-184.
22. Y. Gao, J. M. Klunder, R. M. Hanson, H. Masamune, S. Y. Ko, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
23. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
24. See the Supporting Information.
25. CDCC 721047 (1a), 721048 (1b), 721049 (2), and 721050 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
26. The selectivity of this reaction was substrate-controlled; subsequent efforts to modify the product ratio by using the Sharpless asymmetric dihydroxylation protocol were thwarted by this strong substrate bias.
27. Y. Gao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538-7539.
28. G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, Chem. Commun. 1999, 215-216.
29. C. Thibaudeau, J. Plavec, J. Chattopadhyaya, J. Org. Chem. 1998, 63, 4967-4984.
30. Gaussian03 (Revision D.01): M. J. Frisch et al., Gaussian, Inc., Wallingford, CT, 2004.