Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4770-4779

  Fernández Megía, Eduardo ^a   Iglesias Pintos, José M ^a   Sardina, F Javier ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343219772     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970277q     Document Type: Article

References (61)

1. O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford, 1991; Vol. 1, pp 398-399.
2. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
3. (a) Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566.
4. (b) Rubottom, G. M.; Kim, C. J. Org. Chem. 1983, 48, 1550.
5. (c) Buckley, T. F., III; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157.
6. (d) Knudsen, C. G.; Rapoport, H. J. Org. Chem. 1983, 48, 2260.
7. Creary, X. J. Org. Chem. 1987, 52, 5026.
8. (a) Barluenga, J.; Llavona, L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1991, 297.
9. (b) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696 and references therein.
10. Fernandez-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643.
11. (a) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859.
12. (b) Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164.
13. Brewster, J. H.; Ciotti, C. J., Jr. J. Am. Chem. Soc. 1955, 77, 6214.
14. 5
15. (a) Posner, G. H.; Lentz, C. M. J. Am. Chem. Soc. 1979, 101, 934.
16. (b) Brooks, J. J.; Rhine, W.; Stucky, G. D. J. Am. Chem. Soc. 1972, 94, 7339.
17. (c) Taft, R. W.; Anvia, F.; Gal, J.-F.; Walsh, S.; Capon, M.; Holmes, M. C.; Hosn, K.; Oloumi, G.; Vasanwala, R.; Yazdani, S. Pure Appl. Chem. 1990, 62, 17.
18. (d) Staley, R. H.; Beauchamp, J. L. J. Am. Chem. Soc. 1975, 97, 5920.
19. Correa, J. F.; Fernádez-Megí, E.; Sardina, F. J. Unpublished results.
20. 4 (80:20, 100), DIBAL-H (91:9, 70), K-Selectride (>99:1, 45), Super-Hydride (>99:1, 100), where 6 was always the major product.
21. (a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
22. (b) Seco, J. M.; Latypov, Sh.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 1994, 35, 2921.
23. (c) Seco, J. M.; Latypov, Sh.; Quiñoá, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107.
24. (d) Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504.
25. (e) Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569.
26. The observed stereoselection is consistent with the Felkin-Anh rule for reductions occurring through a nonchelated transition state: Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis; VCH: New York; 1991; pp 47-52.
27. [(Methoxymethoxy)methyl]lithium was prepared by following a literature procedure: Johnson, C. R.; Medich, J. R. J. Org. Chem. 1988, 53, 4131.
28. [p-[(tert-Butyldimethylsilyl)oxy]phenyl]lithium was prepared following a literature procedure: Kurokawa, N.; Ohfune, Y. Tetrahedron 1993, 49, 6195.
29. 2Me group α to the N-Pf always appears at higher field (∼0.4 ppm.) than the one at position β in N-Pf aspartic acid diesters, due to the shielding effect of the fluorenyl ring: Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068 and ref 6. The disappearance of the lower field methoxyl singlet when 9 (δ 3.72 and 3.29 ppm) and 20 (δ 3.54 and 3.18 ppm) are transformed into the corresponding ketones [i.e., 10a, δ 3.28 ppm; 10c, δ 3.19 ppm; 21a, δ 3.28 ppm; 21d, δ 3.16 ppm) provides further proof of the regiochemistry of the reaction.
30. Correa, J. F.; Sardina, P. J. Unpublished results.
31. (a) Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.
32. (b) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024 and references therein.
33. (a) Benz, F.; Knüsel, F.; Nüesch, J.; Treichler, H.; Voser, W.; Nyfeler, R.; Keller-Schierlein, W. Helv. Chim. Acta 1974, 57, 2459.
34. (b) Traber, R.; Keller-Juslén, C.; Loosli, H.-R.; Kuhn, M.; von Wartburg, A. Helv. Chim. Acta 1979, 62, 1252.
35. (a) Balkovec, J. M.; Black, R. M.; Hammond, M. L.; Heck, J. V.; Zambias, R. A.; Abruzzo, G.; Bartizal, K.; Kropp, H.; Trainor, C.; Schwartz, R. E.; McFadden, D. C.; Nollstadt, K. H.; Pittarelli, L. A.; Powles, M. A.; Schmatz, D. M. J. Med. Chem. 1992, 35, 194.
36. (b) Bouffard, F. A.; Zambias, R. A.; Dropinski, J. F.; Balkovec, J. M.; Hammond, M. L.; Abruzzo, G. K.; Bartizal, K. F.; Marrinan, J. A.; Kurtz, M. B.; McFadden, D. C.; Nollstadt, K. H.; Powles, M. A.; Schmatz, D. M. J. Med. Chem. 1994, 37, 222.
37. (c) Debono, M.; Turner, W. W.; LaGrandeur, L.; Burkhardt, F. J.; Nissen, J. S.; Nichols, K. K.; Rodriguez, M. J.; Zweifel, M. J.; Zeckner, D. J.; Gordee, R. S.; Tang, J.; Parr, T. R., Jr. J. Med. Chem. 1995, 38, 3271 and references therein.
38. Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673.
39. Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396.
40. 1-Ethoxy-1-lithioethene was prepared by following a literature procedure: (a) Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913. (b) Soderquist, J. A.; Hsu, G. J.-H. Organometallics 1982, 1, 830.
41. 1-Ethoxy-1-lithioethene was prepared by following a literature procedure: (a) Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913. (b) Soderquist, J. A.; Hsu, G. J.-H. Organometallics 1982, 1, 830.
42. Carter, H. E.; Clark, R. K., Jr.; Kohn, P.; Rothrock, J. W.; Taylor, W. R.; West, C. A.; Whitfield, G. B.; Jackson, W. G. J. Am. Chem. Soc. 1954, 76, 566.
43. Nakanishi, K.; Ito, T.; Hirata, Y. J. Am. Chem. Soc. 1954, 76, 2845.
44. Brockmann, H.; Musso, H. Chem. Ber. 1955, 88, 648.
45. (a) Borders, D. B.; Hausmann, W. K.; Wetzel, E. R.; Patterson, E. L. Tetrahedron Lett. 1967, 4187.
46. (b) Borders, D. B.; Sax, K. J.; Lancaster, J. E.; Hausmann, W. K.; Mitscher, L. A.; Wetzel, E. R.; Patterson, E. L. Tetrahedron 1970, 26, 3123.
47. (c) Kawakami, Y.; Yamasaki, K.; Nakamura, S. J. Antibiot. 1981, 34, 921.
48. Kido, Y.; Furuie, T.; Suzuki, K.; Sakamoto, K.; Yokoyama, Y.; Uyeda, M.; Kinjyo, J.; Yahara, S.; Nohara, T.; Shibata, M. J. Antibiot. 1987, 40, 1698.
49. (a) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413.
50. (b) Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417.
51. (c) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690.
52. (d) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1976, 49, 3611.
53. Kinoshita, M.; Suzuki, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2375.
54. Kusumoto, S.; Imaoka, S.; Kambayashi, Y.; Shiba, T. Tetrahedron Lett. 1982, 23, 2961.
55. The use of 3-Å molecular sieves was necessary to avoid the presence of around 10-30% of recovered ketone (21b) in the crude reaction product, probably due to the formation, in part, of the corresponding hydrate.
56. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
57. (b) Brady, S. F.; Varga, S. L.; Freidinger, R. M.; Schwenk, D. A.; Mendlowski, M.; Holly, F. W.; Veber, D. F. J. Org. Chem. 1979, 44, 3101.
58. (c) Brady, S. F.; Freidinger, R. M.; Paleveda, W. J.; Colton, C. D.; Homnick, C. F.; Whitter, W. L.; Curley, P.; Nutt, R. F.; Veber, D. F. J. Org. Chem. 1987, 52, 764.
59. 3N lead to the formation of several byproducts.
60. Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017.
61. 2/hexane) and purification of the mother liquors by column cromatography (conditions in ref 6) afforded 9 (93% combined yield) in a ratio of diastereomers 20:1.