Enantioselective syntheses of trans-3,4-difluoropyrrolidines and investigation of their applications in catalytic asymmetric synthesis

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 9771-9779

  Marson, Charles M ^a   Melling, Robert C ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CATALYST SELECTIVITY; FLUORINE; SYNTHESIS (CHEMICAL);

BENZALDEHYDES; CHIRALITY; ENANTIOSELECTIVE SYNTHESIS; EPOXIDATIONS;

NITROGEN COMPOUNDS;

1 N OCTYLPYRROLIDINE 3,4 DIOL; 1 PHENYLPYRROLIDINE 3,4 DIOL; 3,4 DIACETOXY 1 (4 IODOPHENYL)PYRROLIDINE 2,5 DIONE; 3,4 DIACETOXY 1 N OCTYLPYRROLIDINE 2,5 DIONE; 3,4 DIFLUOROPYRROLIDINE; BENZALDEHYDE; FLUORINE; ORGANOFLUORINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION;

CATALYSIS; MOLECULAR CONFORMATION; PYRROLIDINES; STEREOISOMERISM;

EID: 28044458136     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0513414     Document Type: Article

References (63)

1. (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bio-organic Chemistry; Wiley: New York, 1991.
2. (b) Wilkinson, J. A. Chem. Rev. 1992, 92, 505-519.
3. (a) Vlahakis, J. Z.; Wand, M. D.; Lemieux, R. P. J. Am. Chem. Soc. 2003, 125, 6862-6863.
4. (b) Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4217-4235.
5. (c) Liu, H.; Nohira, H. Liq. Cryst. 1996, 581-586.
6. (a) Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 9262-9263.
7. (b) Yoder, N. C.; Kumar, K. Chem. Soc. Rev. 2002, 31, 335-341.
8. (a) Aoloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society Symposium Series; American Chemical Society: Washington, DC, 1996; Vol. 639, pp 26-41.
9. (b) McCarthy, J. A.; Sunkara, P. S.; Matthews, D. P.; et al. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society Symposium Series; American Chemical Society: Washington, DC, 1996; Vol. 639, pp 246-264.
10. Hertek, L. W.; Kroin, J. S.; Grossman, C. S. et al. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society Symposium Series; American Chemical Society: Washington, DC, 1996; Vol. 639, pp 265-278.
11. Namchuk, M.; Braun, C.; McCarter, J. D.; Withers, S. G. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society Symposium Series; American Chemical Society: Washington, DC, 1996; Vol. 639, pp 279-293.
12. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661-692.
13. Bouzard, D.; Dicesare, P.; Essiz, M.; Jacquet, J. P.; Kiechel, J. R.; Remuzon, P.; Weber, A.; Oki, T.; Masuyoshi, M.; Kessler, R. E.; Fungtomc, J.; Desiderio, J. J. Med. Chem. 1990, 33, 1344-1352.
14. Kun, E.; Kirsten, E.; Sharma, M. L. Proc. Natl. Acad. Sci. U.S.A 1977, 74, 4942-4946.
15. Craig, N. C.; Chen, A.; Suh, K. H.; Klee, S.; Mellau, G. C.; Winnewisser, B. P.; Winnewisser, M. J. Am. Chem. Soc. 1997, 119, 4789-4790.
16. (a) Holmgren, S. K.; Taylor, K. M.; Bretcher, L. E.; Raines, R. T. Nature 1998, 392, 666-667.
17. (b) Holmgren, S. K.; Bretcher, L. E.; Taylor, K. M.; Raines, R. T. Chem. Biol. 1999, 6, 63-70.
18. Rzepa, H. S.; O'Hagan, D. Chem. Commun. 1997, 645-652.
19. Hougham, G. G.; Cassidy, P. E.; Johns, K.; Davidson, T. Fluoropolymers: Synthesis and Properties; Kluwer Academic: Norwell, MA, 1999.
20. Plenio, H.; Diodone, R.; Badura, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 156-158.
21. For a single example of a racemic uic-difluoro-2,3-dihydrobenzo-[b]furan, see: Ruzziconi, R.; Sebastiani, G. V. J. Heterocycl. Chem. 1980, 17, 1147-1148.
22. For meso-difluorides, see: (a) Hudlicky, M. J. Fluorine Chem. 1987, 36, 373-384.
23. (b) Baklouti, A.; El Gharbi, R. J. Fluorine Chem. 1979, 13, 297-314.
24. (c) Patrick, T. B.; Khazaeli, S.; Nadji, S.; Hering-Smith, K.; Reif, D. J. Org. Chem. 1993, 58, 705-708.
25. (d) Olah, G. A.; Welch, J. T.; Vankar, Y. D.; Nojima, M.; Kerekes, I.; Olah, G. A. J. Org. Chem. 1979, 44, 3872-3881.
26. For the synthesis of (±)-erythro- and (±)-threo-9,10- difluorostearic acids, see: Tavasli, M.; O'Hagan, D.; Pearson, C.; Petty, M. C. Chem. Commun. 2002, 1226-1227.
27. (a) Marson, C. M.; Melling, R. C. J. Chem. Soc., Chem. Commun. 1998, 1223-1234.
28. (b) This method has been used to prepare both enantiomers of 3,4-difluoropyrrolidine and its 1-benzyl derivative: Caldwell, C. G.; Chen, P.; He, J. F.; Parmee, E. R.; Leiting, B.; Marsilio, F.; Patel, R. A.; Wu, J. K.; Eiermann, G. J.; Petrov, A.; He, H. B.; Lyons, K. A.; Thornberry, N. A.; Weber, A. E. Bioorg. Med. Chem. Lett. 2004, 14, 1265-1268.
29. Nicoletti, M.; O'Hagan, D.; Slawin, A. M. Z. J. Am. Chem. Soc. 2005, 127, 482-483.
30. Rozen, S.; Brand, M. J. Org. Chem. 1986, 51, 3607-3611.
31. Sato, M.; Hirokawa, T.; Hattori, A.; Toyota, A.; Kaneko, C. Tetrahedron: Asymmetry 1994, 5, 975-980.
32. (a) Middleton, W. J. J. Org. Chem. 1975, 40, 574-578.
33. (b) Hudlicky, M. Org. React. 1988, 35, 513-637.
34. Shellhamer, D. F.; Austine, D. T.; Gallego, K. M.; Ganesh, B. R.; Hanson, A. A.; Hanson, K. A.; Henderson, R. D.; Prince, J. M.; Heasley, V. L. J. Chem. Soc., Perkin Trans. 2 1995, 861-866.
35. (a) Burmakov, A. I.; Motnyak, L. A.; Kunshenko, B. V.; Alexeva, L. A.; Yagupolskii, L. M. J. Fluorine Chem. 1981, 19, 151-161.
36. 2, see: Syvret, R. G.; Vassilaros, D. L.; Parees, D. M.; Pez, G. P. J. Fluorine Chem. 1994, 67, 277-282.
37. (a) Bourson, J.; Oliveros, L. J. Organomet. Chem. 1982, 229, 77-84.
38. (b) Nagel, U. Angew. Chem., Int. Ed. Engl. 1984, 23, 435-436.
39. Shriner, R. L.; Furrow, C. L. Org. Synth. 1955, 35, 49-51.
40. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326-3343.
41. (a) Langlois, N.; Rojas, A. Tetrahedron Lett. 1993, 34, 2477-2480.
42. (b) Pedregal, C.; Ezquerra; Escribano, A.; Carreño, M. C.; Ruano, J. L. G. Tetrahedron Lett. 1994, 35, 2053-2056.
43. Skarzewski, J.; Gupta, A. Tetrahedron: Asymmetry 1997, 8, 1861-1867.
44. Prasad, A. S. B.; Kanth, J. V. B.; Periasamy, M. Tetrahedron 1992, 48, 4623-4628.
45. Gottlieb, A. A.; Fujita, Y.; Udenfriend, S.; Witkop, B. Biochemistry 1965, 4, 2507-2513.
46. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457-461.
47. Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Perkin Trans. 1 1987, 993-1004.
48. Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43-45.
49. (a) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621-622.
50. (b) Armstrong, A.; Ahmed, G.; Dominguez-Fernandez, B.; Hayter, B. R.; Wailes, J. S. J. Org. Chem. 2002, 67, 8610-8617.
51. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111-7115.
52. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
53. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
54. (b) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 106-113.
55. Reitsema, R. H. J. Am. Chem. Soc. 1949, 71, 2041-2043.
56. Parkes, C. J. Chem. Soc. 1923, 123, 663-669.
57. Feit, P. W. J. Med. Chem. 1964, 7, 14-17.
58. Seebach, D.; Kalinowski, H. O.; Bastani, B.; Crass, G.; Daum, H.; Dorr, H.; Dupreez, N. P.; Ehrig, V.; Langer, W.; Nussler, C.; Oei, H. A.; Schmidt, M. Helv. Chim. Acta 1977, 60, 301-325.
59. Adiyaman, M.; Khanapure, S. P.; Hwang, S. W.; Rokach, J. Tetrahedron Lett. 1995, 36, 7367-7370.
60. McCaig, A. E.; Meldrum, K. P.; Wightman, R. H. Tetrahedron 1998, 54, 9429-9446.
61. Rubin, L. J.; Lardy, H. A.; Fischer, H. O. L. J. Am. Chem. Soc. 1952, 74, 425-428.
62. Scheurer, A.; Mosset, P.; Saalfrank, R. W. Tetrahedron: Asymmetry 1997, 8, 1243-1251.
63. Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657-1660.