Selectfluor as a nucleofuge in the reactions of azabicyclo[n.2.1]alkane β-halocarbamic acid esters (n = 2,3)

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2122-2129

  Krow, Grant R ^a   Gandla, Deepa ^a   Guo, Weiwei ^a   Centafont, Ryan A ^a   Lin, Guoliang ^a   DeBrosse, Charles ^a   Sonnet, Philip E ^a   Ross III, Charles W ^b   Ramjit, Harri G ^b   Cannon, Kevin C ^c  

^a Temple University   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOCARBAMIC ACID ESTERS; SELECTFLUOR;

HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

ESTERS;

BROMINE; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CHLORINE; FLUORINE DERIVATIVE; HALIDE; HALOALCOHOL; HALOKETONE; HEPTANE; HYDROXYL GROUP; MERCURY DERIVATIVE; OCTANE; SELECTFLUOR; SODIUM BROMIDE; SODIUM CHLORIDE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

AZABICYCLO COMPOUNDS; CARBAMATES; DIAZONIUM COMPOUNDS; HYDROCARBONS, HALOGENATED; HYDROLYSIS;

EID: 41849135809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702155v     Document Type: Article

References (54)

1. (a) Krow, G. R.; Lin, G.; Yu, F. J. Org. Chem. 2005, 70, 590-595.
2. (b) Jenkins, C. L.; Lin, G.; Duo, J.; Rapolu, D.; Guzei, I. A.; Raines, R. T.; Krow, G. R. J. Org. Chem. 2004, 69, 8565-8573.
3. (c) Krow, G. R.; Lin, G.; Rapolu, D.; Fang, Y.; Lester, W.; Herzon, S. B.; Sonnet, P. E. J. Org. Chem. 2003, 68, 5292-5299.
4. (d) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259-1262.
5. (e) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Christian, H.; Shaw, D. A.; Yuan, J. J. Org. Chem. 1998, 63, 8558-8560.
6. (f) Krow, G. R.; Lester, W. S.; Liu, N.; Yuan, J.; Hiller, A.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Cannon, K. J. Org. Chem. 2001, 66, 1811-1817.
7. (g) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Liu, N.; Yuan, J.; Duo, J.; Herzon, S. B.; Nguyen. Y.; Zacharias, D. J. Org. Chem. 2001, 66, 1805-1810.
8. (a) Krow, G. R.; Lin, G.; Moore, K. P.; Thomas, A. M.; DeBrosse, C.; Ross, C. W., III; Ramjit, H. G. Org. Lett. 2004, 6, 1669-1672.
9. (b) Krow, G. R.; Lin, G.; Yu, F.; Sonnet. P. E. Org. Lett. 2003, 5, 2739-2741.
10. For reviews of reactions with Selectfluor, see: (a) Singh, R. P.; Shreeve, J. M. Acc. Chem. Res. 2004, 37, 31-44.
11. (f) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C.-H. Angew. Chem., Int. Ed. 2005, 44, 192-212.
12. Throughout this paper, we have chosen to use synlanti nomenclature to identify the stereochemistry of substituents on the non-nitrogen-containing bridges. This is to avoid the use of exolendo nomenclature, confusing to those accustomed to naming the related all-carbon-bridged bicyclic structures. The bridge with the nitrogen heteroatom is always the main bridge of highest priority before the bridge with fewest members. Thus, all substituents anti to nitrogen are endo, even when pointed toward a methylene bridge. Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; John Wiley & Sons, Inc.: New York, 1991; pp 49-50.
13. Krow, G. R.; Huang, Q.; Lin, G.; Centafont, R. A.; Thomas, A. M.; Gandla, D.; DeBrosse, C.; Carroll, P. J. J. Org. Chem. 2006, 71, 2090-2098.
14. Levi, I.; Blondal, H.; Weed, J. W. R.; Frosst, A. C.; Reilly, H. C.; Schmid, F. A.; Sugira, K.; Tarnowski, G. S.; Stock, C. C. J. Med. Chem. 1965, 8, 715-718.
15. (a) Raasch, M. S. J. Org. Chem. 1975, 40, 161-172.
16. (b) Hursthouse, M. B.; Malik, K. M. A.; Hibbs, D. E.; Roberts, S. M.; Seago, A. J. H.; Sik, V.; Storer, R. J. Chem. Soc., Perkin Trans. 1 1995, 2419-2425.
17. For N-alkyl derivatives, see: (a) Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334.
18. (b) Mitch, C. H.; Quimby, S. J. Patent WO 00/75140 A1, 2000.
19. (c) Sosonyuk, S. E.; Bulanov, M. N.; Leshcheva, I. F.; Zyk, N. V. Russ. Chem. Bull. 2002, 51, 1254-1261.
20. (d) Bulanov, M. N.; Sosonyuk, S. E.; Zyk, N. V.; Zefirov, N. S. Russ. J. Org. Chem. 2003, 39, 415-421.
21. (a) Krow, G. R.; Shaw, D. A.; Jovais, C. S.; Ramjit, H. G. Synth. Commun. 1983, 13, 575-579.
22. (b) Krow, G. R.; Raghavachari, R.; Shaw, D. A.; Zacharias, D. E. Trends Heterocycl. Chem. 1990, 1, 1-7.
23. (c) Krow, G. R.; Lee, Y. B.; Raghavachari, R.; Szczepanski, S. W.; Alston, P. V. Tetrahedron 1991, 47, 8499-8514.
24. (d) Krow, G. R.; Shaw, D. A.; Szczepanski, S.; Ramjit, H. G. Synth. Commun. 1984, 14, 429-433.
25. For 4,8-disubstituted N-alkyl-2-azabicyclo[3.2.1]octanes, see: ref 11 and Hutchins, R. O.; Rua, L., Jr. J. Org. Chem. 1975, 40, 2567-2568.
26. Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334.
27. For 8-anti-hydroxy-6-azabicyclo[3.2.1]octanes: Peduncularine: (a) Roberson, C. W.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 11342-11348.
28. (b) Roberson, C. W.; Woerpel, K. A. Org. Lett. 2000, 2, 621-623.
29. Norsecurinine skeleton: (c) Magnus, P.; Rodriguez-Lopez, J.; Mulholland, K.; Matthews, I. J. Am. Chem. Soc. 1992, 114, 382-383.
30. Actinobolamine: (d) Holmes, A. B.; Kee, A.; Ladduwahetty, T.; Smith, D. F. J. Chem. Soc., Chem. Commun. 1990, 1412-1414.
31. For 8-syn-hydroxy-6-azabicyclo[3.2.1]-octanes: Peduncularine: (e) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588-2595.
32. (f) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581-1584.
33. (g) Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333-2337.
34. (h) Washburn, D. G.; Heidebrecht, R. W., Jr.; Martin, S. F. Org. Lett. 2003, 5, 3523-3525.
35. Catharanthine byproduct: (i) Trost, B. M.; Godleski, S. A.; Belletire, J. L. J. Org. Chem. 1979, 44, 2052-2054.
36. Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; DeBrosse, C.; Sonnet, P. E.; Ross, C. W., III; Ramjit, H. G.; Carroll, P. J.; Cannon, K. C. J. Org. Chem. 2008, 73, 2114-2121.
37. (a) For unsuccessful nucleophilic displacement reactions of a 7-anti-bromo-2,6-ethanobridged-2-azabicyclo[2.2.1]heptane, see: Wilson, S. R.; Sawicki, R. A.; Huffman, J. C. J. Org. Chem. 1981, 46, 3887-3891.
38. (b) However, for successful nucleophilic displacements with 8-anti-bromo-N-benzyl-2-azabicyclo[2.2.1]heptane with retention of stereochemistry, see ref 8a.
39. (c) Ni(0)-catalyzed couplings of arylboronic acids with N-Boc-7-anti-bromo-2-azabicyclo[2.2.1]heptane give 7-synlanti-aryl mixtures. Malpass, J. R.; Handa, S.; White, R. Org. Lett. 2005, 7, 2759-2762.
40. (a) Biamonte, M. A.; Vasella, A. Helv. Chim. Acta 1998, 81, 695-717.
41. (b) Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. Tetrahedron 1996, 52, 12613-12622.
42. (c) Carosati, E.; Sciabola, S.; Cruciani, G. J. Med. Chem. 2004, 47, 5114-5125.
43. (d) Shimoni, L.; Glucker, J. P. Struct. Chem. 1994, 5, 383-397.
44. For reviews, see: (e) Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573.
45. (f) Dunitz, J. D.; Taylor, R. Chem-EUK J. 1997, 3, 89-98.
46. (g) Jackel, C.; Koksch, B. Eur. J. Org. Chem. 2005, 4483-4503.
47. (a) For an example of intramolecular nucleophilic displacement of an 8-syn-bromine in a 6-azabicyclo[3.2.1]octane, see: Davies, H. M. L.; Cao, G. Tetrahedron Lett. 1998, 39, 5943-5946.
48. Mercury salt oxidations of alcohols are not common, (a) McKillop, A.; Young, D. W. Synth. Commun. 1977, 7, 467-474.
49. (b) Habibi, M. H.; Farhadi, S. Pol. J. Chem. 2004, 78, 741-744.
50. For a review of the reactions with Deoxo-Fluor and the related DAST (diethylaminosulfur trifluoride), see: Singh, R. P.; Shreeve, J. M. Synthesis 2002, 2561-2578.
51. Reactions of N-protected amino alcohols with DAST have been observed both with and without neighboring group participation, (a) De Jonghe, S.; Overmeire, I. V.; Van Calenbergh, S.; Hendrix, C.; Busson, R.; de Keukeleire, D.; Herdewijn, P. Eur. J. Org. Chem. 2000, 3177-3183.
52. (b) Hallett, D. J.; Gerhard, U.; Goodacre, S. C.; Hitzel, L.; Sparey, T. J.; Thomas, S.; Rowley, M.; Ball, R. G. J. Org. Chem. 2000, 65, 4984-4993.
53. (c) Golubev, A. S.; Schedel, H.; Radies, G.: Sieler, J.; Burger, K. Tetrahedron Lett. 2001, 42, 7941-7944.
54. Haufe, G.; Rolle, U.; Kleinpeter, E.; Kiviloski, J.; Rissanen, K. J. Org. Chem. 1993, 58, 7084-7088. Halogen substitution in the conversion of anti,anti-2,6-dibromo-N-cyano-9-azabicyclo[3.3.1] nonane (i) and anti, anti-2,5-dibromo-N-cyano-9- azabicyclo[4.2.1]nonane (ii) to the corresponding N-acetyl-2,6- or 2,5-diacetates using silver acetate has been reported to occur with retention at one carbon and inversion at another. The NMR and symmetry properties of each amide structure are more consistent with a pair of N-acetyl conformational isomers having either two retained configurations or two inverted configurations. Our results that show the importance of nitrogen participation in bridged azabicyclic systems suggest doubly retained anti configurations iii and iv for the diacetates. Dr. Haufe is currently reinvestigating this problem (personal communication). (Graph Presented)