Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3- hydroxypipecolic acid from a chiral n-imino-2-phenyl-1,2-dihydropyridine intermediate

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 2077-2080

  Lemire, Alexandre ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYPIPECOLIC ACID; CHEMICAL EQUATIONS; DIHYDROPYRIDINES; HETERO-DIELS-ALDER REACTIONS; PIPECOLIC ACID; STEREOSELECTIVE SYNTHESIS;

AMINO ACIDS; ORGANIC ACIDS; OXYGEN; PYRIDINE; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

1 TRIFLUOROACETYL 2 PHENYL 1,2,3,6 TETRAHYDROPYRIDIN 3 YL ACETATE; 2 PHENYL 1,2,3,6 TETRAHYDROPYRIDIN 3 OL; 3 HYDROXYPIPECOLIC ACID; ACID ANHYDRIDE; N IMINO 2 PHENYL 1,2 DIHYDROPYRIDINE; N IMINOPYRIDINIUM SALT; PIPECOLIC ACID; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; TRIFLUOROMETHANE SULFONIC ANHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; HYDROXYLATION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

DIHYDROPYRIDINES; MOLECULAR STRUCTURE; PIPECOLIC ACIDS; STEREOISOMERISM;

EID: 77949864262     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902527s     Document Type: Article

References (99)

1. (a) Isolation: Morrison, R. I. Biochem J. 1953, 53, 474.
2. (b) Racemic synthesis: Ladenburg, A. Ber. 1891, 24, 640.
3. (c) First resolution: Mende, F. Ber Dtsch. Chem. Ges. 1896, 29, 2887.
4. For biosynthetic studies, see: (a) Wickwire, B. M.; Harris, C. M.; Harris, T. M.; Broquist, H. P. J. Biol. Chem. 1990, 265, 14742.
5. (b) Zabriskie, T. M.; Kelly, W. L.; Liang, X. J. Am. Chem. Soc. 1997, 119, 6446 and references cited therein.
6. Pastuszak, I.; Molyneux, R. J.; James, L. F.; Elbein, A. D. Biochemistrv 1990, 29, 1886.
7. Portoghese, P. S.; Pazdemik, T. L.; Kuhn, W. L.; Hite, G.; Shafi'ee, A. J. Med. Chem. 1968, 11, 12.
8. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031.
9. Swindells, D. C. N.; White, P. S.; Findlay, J. A. Can. J. Chem. 1978, 56, 2491.
10. For reviews, see: (a) Agami, C.; Couty, F.; Puchot-Kadouri, C. Synlett 1998, 449.
11. (b) Couty, F. Amino Acids 1999, 16, 297.
12. (c) Rutjes, F. R. T. T.; Wolf, L. B.; Schoemaker, H. E. J. Chem. Soc. Perkin Trans. 1. 2000, 4197.
13. (d) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629.
14. (e) Kadouri-Puchot, C.; Comesse, S. Amino Acids 2005, 29, 101.
15. (a) Ng-Youn-Chen, M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. Ogr. Chem. 1994, 59, 2075.
16. (b) Hockless, D. C. R.; Mayadunne, R. C.; Wild. S. B. Tetrahedron: Asymmetry 1995, 6, 3031.
17. (c) Sánchez-Sancho, F.; Herradön, B. Tetrahedron: Asymmetry 1998, 9, 1951.
18. (d) Kim, C.-S.; Lee, I.-S.; Chung, N.; Bang, W.-G. J. Microbiol. Biotechnol. 2001, 11, 217.
19. (e) Liljeblad, A.; Lindborg, J.; Kanerva, A.; Katajisto, J.; Kanerva, L. T. Tetrahedron Lett. 2002, 43, 2471.
20. (f) Watanabe, L. A.; Haranaka, S.; Jose, B.; Yoshida, M.; Kato, T.; Morigushi, M.; Soda, K.; Nishino, N. Tetrahedron: Asymmetry 2005, 16, 903.
21. (a) Fujii, T.; Miyoshi, M. Bull. Chem. Soc., Jpn. 1975, 48, 1341.
22. (b) Aketa, K.-i.; Terashima, S.; Yamada, S.-i. Chem. Pharm. Bull. 1976, 24, 621.
23. (c) Kisfaludy, L.; Korenczki, F.; Kathó. A. Synthesis 1982, 163.
24. (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769.
25. (b) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488.
26. (c) Agami, C.; Kadouri-Puchot, C.; Kizirian, J.-C. Synth. Commun. 2000, 30, 2565.
27. (d) Hou, D.-R.; Hung, S.-Y.; Hu, C.-C. Tetrahedron: Asymmetry 2005, 16, 3858.
28. (e) Chang, M.-Y.; Kung, Y.-H.; Wu, T.-C. Heterocycles 2006, 68, 2365.
29. Fadel, A.; Lahrache, N. J. Org. Chem. 2007, 72, 1780.
30. (g) Chattopadhyay, S. K.; Biswas, T.; Biswas, T. Tetrahedron Lett. 2008, 49, 1365.
31. (a) Fernández-García, C.; McKervey, M. A. Tetrahedron; Asymmstry 1995, 6, 2905.
32. (b) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998. 39, 5347.
33. (c) Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656.
34. (d) Wilkinson, T. J.; Stehle, N. W.; Beak, P. Org. Lett. 2000, 2, 155.
35. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762.
36. (f) Teoh, E.; Campi, E. M.; Jackson, W. R.; Robinson, A. J. Chem. Commun. 2002, 978.
37. (g) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779.
38. (h) Rogers L. M-A.; Rouden, J.; Lecomte, L.; Lane, M.-C. Tetrahedron Lett. 2003, 44, 3047.
39. (a) Calmes, M.; Escale, F.; Rolland, M.; Martinez, J. Tetrahedron: Asymmetry 2003, 14, 1685.
40. (b) Martin, J.; Plaquevent, J.-C; Maddaluno, J.; Rouden, J.; Lasne, M.-C. Eur. J. org. Chem. 2009, 5414.
41. (a) Aroyan, C. E.; Vasbinder, M. M.; Miller, S. J. Org. Lett. 2005, 7, 3849.
42. (b) Cheong, P. H.-Y.; Zhang, H.; Thayumanavan, R.; Tanaka, F.; Houk, K. N.; Barbas, C. F. Org. Lett. 2006, 8, 811.
43. (c) Yoshimura, Y.; Ohara, C.; Miyagawa, T.; Takahata, H. Heterocycles 2009, 77, 635. For the utilization of L-pipecohc acid N-oxides derivatives as ligands in the indiumcatalyzed allylation of ketones, see:
44. (d) Zhang, X.; Chen, D.; Liu, X.; Feng, X. J. Org. Chem. 2007, 72, 5227.
45. (a) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866.
46. (b) Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. Tetrahedron: Asymmetrv 1993, 4, 625.
47. (c) Greek, C.; Ferreira, F.; Genet, J. P. Tetrahedron Lett. 1996, 37, 2031.
48. (d) Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001.
49. (e) Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
50. (f) Scott, J. D.; Tippie, T. N.; Williams, R. M. Tetrahedron Lett. 1998, 39, 3659.
51. (g) Sugisaki, C. H.; Carroll, P. J.; Correia. C. R. D. Tetrahedron Lett. 1998, 39, 3413.
52. (h) Horikawa, M.; Busch-Peterson, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
53. (i) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2000, 41, 7033.
54. (j) Scott, J. D.; Williams, R. M. Tetrahedron Lett. 2000, 41, 8413.
55. (k) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 2001, 42, 5223.
56. (l) Kumar, P.; Bodas, M. S. J. Org. Chem. 2005, 70, 360.
57. (m) Liang, N.; Datta, A. J. Org. Chem. 2005, 70, 10182.
58. (n) Alegret, C.; Ginesta, X.; Riera, A. Eur. J. Org. Chem. 2008, 1789.
59. For the synthesis of febrifugme, see: (a) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. J. Org: Ctem. 1999, 64, 6833. For synthesis of other relevant trans-2-substituted-3-hydroxypiperidines, see:
60. (b) Calvez, O.; Chiaroni, A.; Langlois, N. Tetrahedron Lett. 1998, 39, 9447.
61. (c) Enders, D.; Noite, B.; Runsink, J. Tetrahedron: Asymmetry 2002, 13, 587.
62. (d) Bodas, M. S.; Upadhyay, P. K.: Kumar. P. Tetrahedron Lett. 2004, 45, 987.
63. Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2251.
64. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
65. (b) Cowcll, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Curr. Med. Chem. 2004, 11, 2785.
66. (a) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
67. b) Legault, C.; Charette, A.B. J. Am. Chem. Soc. 2003, 125, 6360.
68. (c) Lemire, A.; Grenon, M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517.
69. (d) Lemire, A.; Beaudoin, D.; Grenon, M.; Charette, A. B. J. Org. Chem. 2005, 70, 2368.
70. (e) Lemire, A.; Charette, A. B. Org. Lett. 2005, 7, 2747.
71. (f) Charette, A. B.; Mathieu, S.; Martel, J. Org. Lett. 2005, 7, 5401.
72. (g) Sales, M.; Charette, A. B. Org. Lett. 2005, 7, 5773.
73. (h) Larivée, A.; Charette, A. B. Org. Lett. 2006, 8, 3955.
74. (i) Pocken, T.; Charette, A. B. Org. Lett. 2006, 8, 2985.
75. (j) Barbe, G.; Charette, A. B. J. Am. Chem. Soc. Lett. 130. 13873.
76. (a) Still,W.C. J. Am. Chem. Soc. 1978, 100, 1481.
77. b) Johnson, C. R.; Medien, J. R. J. Org. Chem. 1988, 53, 4131.
78. No regio- or diastereocontrol occurs when organohthium reagents are added to N-iminopyridinium salts.
79. Taguchi, T.; Kasuga, S. Chem. Pharm. Bull. 1965, 13, 241.
80. Cyanide addition to the chiral pyridinium salt 4 was also investigated, with limited, success. Reaction of 4 with trimethylsilyl cyanide in the presence of aluminum chloride resulted in the formation of a new adduct, which proved, too labile for isolation. Chiral amide starting material 3 was recovered, presumably after reversible cyanide liberation and hydrolysis of the pyridinium salt. For related examples, see: (a) Popp, F. D.; Takeuchi, I.; Kant, J.; Hamada, Y. J. Chem. Soc., Chem. Commun. 1987, 1765.
81. (b) Yaguchi, K.; Endo, Y. Tetrahedron Lett. 1999, 40, 7351.
82. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936. For use in hydroxy amino acid synthesis, see:
83. (b) Shioiri, T.; Matsuura, F.; Hamada, Y. Pure Appl. Chem. 1994, 66, 2151. For use in pipecolic acid derivatives, see:
84. (c) Nazih, A.; Schneider, M.-R.; Mann, A. Synlett 1998, 1337.
85. (d) Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231.
86. (e) See ref 14k.
87. (f) Kim, I. S.; Oh, J. S.; Zee, O. P.; Jung, Y. H. Tetrahedron 2007, 63, 2622.
88. Regioselectivity of 1,2- vs 1,4-addition, > 98:2; diastereoselectivity of addition at C-2, > 98:2.
89. Hydrogenation to piperidine failed when a 2-furyl substituent was present at C-2 on the dihydropyridine, instead of the phenyl group shown. The N-debenzylation process led to the opening of the piperidine ring if a more electron-rich furan was present at C-2.
90. Reduction of the amidine chiral auxiliary is readily accomplished with alane (2.5 h). We used the following procedure for alane preparation: Finholt, A. E.; Bond, A. C., Jr.; Schlesinger, H. I. J. Am. Chem. Soc.1947, 69, 1199. Using DIBAL-H instead of alane required, extensive reaction time in dichloromethane, or refluxing the solution in toluene (4 h) to give similar yield, of product.
91. Following this procedure: Hill, R. K.; Prakash, S. R.; Zydowsky, T. M. J. Org. Chem. 1984, 49, 1666.
92. Compound 11 was derived to its methyl ester (lia), which allowed for enantiomeric determination. See the Supporting Information.
93. For precedents on singlet oxygen HDA with dihydropyridines, see: (a) Natsume, M.; Sekine, Y.; Soyagimi, H. Chem. Pharm. Bull. 1978, 26, 2188.
94. (b) Natsume, M.; Wada, M.; Ogawa, M. Chem. Pharm. Bull. 1978, 26, 3364.
95. (c) Natsume, M.; Sekine, Y.; Ogawa, M.; Soyagimi, H.; Kitagawa, Y. Tetrahedron Lett.1979, 20, 3473. For a precedent with, hydride reduction of aminal,see:
96. (d) Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992. 33, 349.
97. Singlet oxygen reacted on the less hindered face of the dihydropyridine ring (>98:2 dr), i.e. anti to the 2-phenyl group (which is forced to be axial by the amidine electron-withdrawing group).
98. (a) Ando, A.; Shioiri, T. Tetrahedron 1989, 45, 4969.
99. (b) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 537.