Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: Application to the synthesis of nicotine analogues

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4017-4026

  Huang, Kun ^a   Merced, Francisco G ^a   Ortiz Marciales, Margarita ^a   Meléndez, Héctor J ^a   Correa, Wildeliz ^a   De Jesús, Melvin ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ESTERS; ETHERS; ETHYLENE; ETHYLENE GLYCOL; GLYCOLS; SYNTHESIS (CHEMICAL);

2-AMINO; AMERICAN CHEMICAL SOCIETY (ACS); ASYMMETRIC REDUCTION; ASYMMETRIC SYNTHESIS; BORANE REDUCTION; CATALYTIC LOADINGS; CHEMICAL EQUATIONS; ENANTIOPURE; ENANTIOSELECTIVE; ENANTIOSELECTIVE REDUCTION; KETOXIMES; OPTIMAL CONDITIONS; PRIMARY AMINES; PYRIDYL; SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

ORGANIC COMPOUNDS;

2 AMINO 2 PYRIDYLETHANOL; BORANE DERIVATIVE; ESTER DERIVATIVE; ETHER DERIVATIVE; ETHYLENE GLYCOL; N ETHYLNORNICOTINE; NICOTINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION;

BORANES; CATALYSIS; ESTERS; ETHERS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; NICOTINE; OXIDATION-REDUCTION; OXIMES; STEREOISOMERISM; VALINE;

EID: 44949109272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800204n     Document Type: Article

References (100)

1. (a) Sine, S. M. Neurobiology 2002, 53, 431-446.
2. (b) Tonder, J. E.; Olesen, P. H. Curr. Med. Chem. 2001, 8, 651.
3. (c) Jensen, A. A.; Frolund, B.; Liljefors, T.; Krogsgaard-Larsen, P. J. Med. Chem. 2005, 48, 4705.
4. (a) Lloyd, G. K.; Williams, M. J. Pharm. Exp. Ther. 2000, 292, 461.
5. (b) Cosford, N. D. P.; Blecher, L.; Herbaut, A.; Mccallum, J. S.; Venier, J. M.; Dawson, H.; Whitten, J. P.; Adams, P.; Chavez-Noriega, L.; Correa, L. D.; Crona, J. H.; Mahaffy, L. S.; Menzaghi, L. S.; Rao, T. S.; Reid, R.; Sacaan, S. I.; Santori, E.; Stauderman, K. A.; Whelan, K.; McDonald, I. A. J. Med. Chem. 1996, 39, 3235.
6. (c) Galzi, J. L.; Changeux, J. P. Neuropharmacology 1995, 34, 563.
7. (a) Breining, S. R. Curr. Top. Med. Chem. 2004, 4, 609.
8. (b) Talley, T. T.; Yalda, S.; Ho, K. Y.; Tor, Y.; Soti, F. S.; Kern, W. R.; Taylor, P. Biochemistry 2006, 45, 8894.
9. (c) Abreo, M. A.; Lin, N. H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A. M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.; Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Williams, M.; Arneric, S. P.; Holladay, M. W. J. Med. Chem. 1996, 39, 817.
10. (d) Newhouse, P. A.; Potter, A.; Lenox, R. H. Med. Chem. Res. 1993, 2, 628.
11. (e) Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villiéras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305.
12. (f) Ayers, J. T.; Xu, R.; Dwoskin, L. P.; Crooks, P. A. AAPS J. 2005, 7, E752.
13. (g) Brennan, M. B. Chem. Eng. News 2000, 78, 23.
14. (a) Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169.
15. (b) Latli, B.; D'Amour, K.; Casida, J. E. J. Med. Chem. 1999, 42, 2227.
16. (c) Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217.
17. (d) Mullen, G.; Napier, J.; Balestra, M.; DeCory, T.; Hale, G.; Macor, J.; Mack, R.; Loch, J.; Wu, E.; Rover, A.; Verhoest, P.; Sampognaro, A.; Phillips, E.; Zhu, Y.; Murray, R.; Griffith, R.; Blosser, J.; Gurley, D.; Machulskis, A.; Zongrone, J.; Rosen, A.; Gordon, J. J. Med. Chem. 2000, 43, 4045.
18. (e) Chelucci, G. Tetrahedron: Asymmetry 2005, 16, 2353.
19. (a) Bachurin, S. O. Med. Res. Rev. 2003, 23, 48.
20. (b) Vernier, J.-M.; El-Abdellaoui, H.; Holsenback, H.; Cosford, N. D. P.; Bleicher, L.; Barker, G.; Bontempi, B.; Chavez-Noriega, L.; Menzaghi, F.; Rao, T. S.; Reid, R.; Sacaan, A. I.; Suto, C.; Washburn, M.; Lloyd, G. K.; McDonald, I. A. J. Med. Chem. 1999, 42, 1684.
21. (a) Schmitt, J. D.; Bencherif, M. In Annual Reports in Medicinal Chemistry; Doherty, A. M., Ed.; Academic Press: New York, 2000; Vol. 35, pp 41-51.
22. (b) Pereira, E. F. R.; Hilmas, C.; Santos, M. D.; Alkondon, M.; Maelicke, A.; Albuquerque, E. X. J. Neurobiol. 2002, 53, 479.
23. Wilkins, H., L., Jr.; Grinevich, V. P.; Ayers, J. T.; Crooks, P. A.; Dwoskin, L. P. J. Pharm. Exp. Ther. 2003, 304.
24. (a) Palmer, A. M. Trends Pharmacol. Sci. 2003, 23, 426.
25. (b) Salomon, A. R.; Marcinowski, K. J.; Friedland, R. P.; Zagorski, M. G. Biochemistry 1996, 35, 13568.
26. (c) Liu, Q.; Zhao, B. Br. J. Pharmacol. 2004, 141, 746.
27. (d) Dickerson, T. J.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8182.
28. Aceto, M. D.; Martin, B. R.; Uwaydah, I. M.; May, E. L.; Harris, L. S.; Izazola-Conde, C.; Deway, W. L.; Bradshaw, T. J.; Vincek, W. C. J. Med. Chem. 1979, 22, 174.
29. (a) Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge, U.R., 2004.
30. (b) Breuer, M.; Ditrich, R.; Habicher, T.; Hauer, B.; Keâeler, M.; Sturmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788.
31. (c) Hieber, G.; Ditrich, R. Chim. Oggi 2001, 19, 16.
32. (d) Franchini, C.; Carocci, A.; Catalano, A.; Cavalluzzi, M. M.; Corbo, F.; Lentini, G.; Scilimati, A.; Tortorella, P.; Camerino, D. C.; Luca, A. J. Med. Chem. 2003, 46, 5238.
33. (e) Abreo, M. A.; Lin, N. H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A. M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.; Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Stephen, M. W.; Arneric, S. P.; Holladay, M. W. J. Med. Chem. 1996, 39, 817.
34. (a) Henderson, K. W. Chem. Commun. 2000, 479.
35. (b) Denolf, B.; Mangelinckx, S.; Tornroos, K. W.; Kimpe, N. D. Org. Lett. 2006, 8, 3129.
36. (c) Tanuwidjaja, J.; Peltier, H. M.; Ellman, J. A. J. Org. Chem. 2007, 72, 626.
37. (d) Bloch, R. Chem. Rev. 1998, 98, 1407.
38. (a) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
39. (b) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
40. (c) Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598.
41. (d) Liu, T. Y.; Cui, H. L.; Jiang, K.; Du, W.; He, Z. Q.; Chen, Y. C. Org. Lett. 2007, 9, 3671.
42. (e) Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Mechiorre, P. Org. Lett. 2007, 9, 1403.
43. (f) Fache, F. S. E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
44. (g) Dickerson, T. J.; Lovell, T.; Meijler, M. M.; Noodleman, L.; Janda, K. D. J. Org. Chem. 2004, 69, 6603.
45. (h) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985.
46. (i) GlushkovV. A.;Tolstikov A. G.;Russ. Chem. Rev. (Engl. Transl.)200473581 and refs. cited therein.
47. (j) Cho, B. T. Tetrahedron2006,62,7621 and refs. cited therein.
48. Kozma, D. CRC Handbook of Optical Resolutions via Diatereomeric Salt Formation 1st ed.;CRC Press LLC: Boca Raton, FL, 2001.
49. (a) JohanssonA.;Contemp. Org. Synth. 199566393 and refs. cited therein.
50. (b) DelouxL.;SrebnikM.;Chem. Rev. 199397763 and refs. cited therein.
51. (c) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
52. (d) Fernández, H.; Hooper, M. W.; Knight, F. I.; Brown, J. M. Chem. Commun. 1997, 173.
53. (e) Fernández, H.; Maeda, R.; Hooper, M. W.; Brown, J. M. Chem. - Eur. J. 2000, 6, 1840.
54. (f) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
55. (a) Bolm, C.; Felder, M. Synlett 1994, 655.
56. (b) Lantos, I.; Flisak, J.; Liu, L.; Matsunoka, R.; Mendelson, W.; Stevenson, D.; Tubman, K.; Tucker, L.; Zhang, W.-Y.; Adams, J.; Sorenson, M.; Garigipati, R.; Erhardt, K.; Ross, S. J. Org. Chem. 1997, 62, 5385.
57. (c) Tillyer, R. D.; Boudreau, C.; Tschaen, D.; Dolling, U.-H.; Reider, P. J. Tetrahedron Lett. 1995, 36, 4337.
58. (d) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607.
59. (e) Shimizu, M.; Tsukamoto, R.; Matsutani, T.; Fujisawa, T. Tetrahedron 1998, 54, 10265.
60. (f) Masui, M.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5195.
61. (g) Cho, B. T.; Ryu, M. H. Bull. Korean Chem. Soc. 1994, 15, 191.
62. (h) Demir, A. S. Pure Appl. Chem. 1997, 69, 105-108.
63. (i) Sakito, Y.; Yoneyoshi, Y.; Suzukamo, G. Tetrahedron Lett. 1988, 29, 223.
64. (a) Itsuno, S.; Sakurai, Y.; Ito, R.; Hirao, A.; Nakahama, S. Bull. Chem. Soc. Jpn. 1987, 60, 395.
65. (b) Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, R. J. Chem Soc., Perkin Trans. 1 1985, 2039.
66. (c) Itsuno, S.; Sakurai, Y.; Shimizu, R.; Ito, R. J. Chem. Soc. Perkin Trans. 1 1990, 1859.
67. (d) Inoue, T.; Sato, D.; Romura, R.; Itsuno, S. Tetrahedron Lett. 1999, 40, 5379.
68. (a) Itsuno, S.; Matsumoto, T.; Sato, D.; Inoue, T. J. Org. Chem. 2000, 65, 5879.
69. (b) Sailes, H. E.; Watts, J. P.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2000, 3362.
70. (c) Fontaine, E.; Namane, C.; Meneyrol, J.; Geslin, M.; Serva, L.; Roussey, E.; Tissandie, S.; Maftouh, M.; Roger, P. Tetrahedron: Asymmetry 2001, 12, 2185.
71. (d) Krzeminski, M. P.; Zaidlewicz, M. Tetrahedron: Asymmetry 2003, 14, 1463.
72. (e) Chu, Y. B.; Shan, Z. X.; Liu, D. J.; Sun, N. N. J. Org. Chem. 2006, 71, 3998.
73. (a) Stepanenko, V.; Ortiz-Marciales, M.; Barnes, C. E.; Garcia, C. Tetrahedron Lett. 2006, 47, 7603.
74. (b) Ortiz-Marciales, M.; De Jesus, M.; Gonzales, E.; Raptis, R. G.; Baran, P. Acta Crystallogr. 2004, C60, 173.
75. (c) Lang, A.; Noth, H.; Schmidt, M. Chem. Ber. 1997, 130, 241.
76. (d) Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880.
77. (e) Tlahuext, H.; Santiesteban, F.; García-Báez, E.; Contreras, R. Tetrahedron: Asymmetry 1994, 5, 1579.
78. (f) Santiesteban, F.; Mancilla, T.; Klaébe, A.; Contreras, R. Tetrahedron Lett. 1983, 24, 759.
79. (g) Brown, J. M.; Guy, C.; Lloyd-Jones, G. C.; Layzell, T. P. Tetrahedron: Asymmetry 1993, 4, 2151.
80. (a) Stepanenko, V.; Ortiz-Marciales, M.; Correa, W.; De-Jesús, M.; Espinosa, S.; Ortiz, L. Tetrahedron: Asymmetry 2006, 17, 112-115.
81. (b) Ortiz-Marciales, M.; Stepanenko, V.; Correa, W.; De Jesús, M.; Espinosa, S. U.S. Patent Application 11/512,599, Aug 30, 2006.
82. (c) Stepanenko, V.; Ortiz-Marciales, M.; De Jesús, M.; Correa, W.; Vázquez, C.; Ortiz, L.; Guzmán, I.; De la Cruz, W. Tetrahedron: Asymmetry 2007, 18, 2738.
83. (a) Huang, X.; Ortiz-Marciales, M.; Huang, R.; Stepanenko, V.; Merced, F. G.; Ayala, A. M.; De Jesús, M. Org. Lett. 2007, 9, 1793.
84. (b) Ortiz-Marciales, M.; Huang, X.; Huang, R.; Stepanenko, V.; De Jesús, M.; Merced, F. G. PCT/US07/76195 Aug 17, 2007.
85. Benjahad, A.; Croisy, M.; Monneret, C.; Bisagni, E.; Mabire, D.; Coupa, S.; Poncelet, A.; Csoka, I.; Guillemont, J.; Meyer, C.; Andries, R.; Pauwels, R.; de Béthune, M. P.; Himmel, D. M.; Das, K.; Arnold, E.; Nguyen, C. H.; David, S.; Grierson, D. S. J. Med. Chem. 2005, 48, 1948.
86. 23
87. Blake, J. A.; Ingold, K. U.; Lin, S.; Mulder, P.; Pratt, D. A.; Sheeller, B.; Walton, J. C. Org. Biomol. Chem. 2004, 2, 415.
88. Mitsunobu, O. Synthesis 1981, 1.
89. Bernotas, R. C.; Cube, R. V. Tetrahedron Lett. 1991, 32, 161.
90. (a) Lawrence, S. A. In Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge, U.K., 2004.
91. (b) Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Keâeler, M.; Sturmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788.
92. (c) Hieber, G.; Ditrich, K. Chim. Oggi 2001, 19, 16.
93. (d) Franchini, C.; Carocci, A.; Catalano, A.; Cavalluzzi, M. M.; Corbo, F.; Lentini, G.; Scilimati, A.; Tortorella, P.; Camerino, D. C.; Luca, A. J. Med Chem. 2003, 46, 5238.
94. (e) Abreo, M. A.; Lin, N. H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A. M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.; Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Stephen, M. W.; Arneric, S. P.; Holladay, M. W. J. Med. Chem. 1996, 39, 817.
95. (a) Henderson, K. W. Chem. Commun. 2000, 479.
96. (b) Denolf, B.; Mangelinckx, S.; Tornroos, K. W.; Kimpe, N. D. Org. Lett. 2006, 8, 3129.
97. (c) Tanuwidjaja, J.; Peltier, H. M.; Ellman, J. A. J. Org. Chem. 2007, 72, 626.
98. Edwards, William, B. J. Heterocycl. Chem. 1975, 12, 413.
99. Ohkawa, S.; Terao, J. S.; Terashita, Z. I.; Shibouta, Y.; Nishikawat, K. J. Med. Chem. 1991, 34, 267.
100. Damaj, M. I.; Glassco, W.; Dukat, M.; May, E. L.; Richard, A.; Martin, B. R. Drug Dev. Res. 1996, 38, 177.