Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid

Journal of Organic Chemistry

Volumn 73, Issue 13, 2008, Pages 5155-5158

  Carlson, Erik C ^a   Rathbone, Lauren K ^a   Yang, Hua ^a   Collett, Nathan D ^a   Carter, Rich G ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL REACTIONS; REACTION KINETICS;

AMERICAN CHEMICAL SOCIETY (ACS); CHEMICAL EQUATIONS; ENANTIO SELECTIVE SYNTHESIS; HETERO ATOMS; MICHAEL ADDITIONS; ORGANOCATALYSIS; PIPERIDINE RINGS; PYRROLIDINE;

SYNTHESIS (CHEMICAL);

ALKALOID; ALKENE; HOMOPIPECOLIC ACID; PELLETIERINE; PIPECOLIC ACID; PIPERIDINE DERIVATIVE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

CATALYSIS; MOLECULAR STRUCTURE; PIPECOLIC ACIDS; PIPERIDINES; PROLINE;

EID: 46849122706     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800749t     Document Type: Article

References (66)

1. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-60.
2. Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. 1997, 36, 2282-316.
3. (a) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-25.
4. (b) McGrath, M. J.; Bilke, J. L.; O'Brien, P. Chem. Commun. 2006, 2607-09, and references cited within.
5. (c) Dieter, R. K.; Topping, C. M.; Kishan, R. C.; Lu, K. J. Am. Chem. Soc. 2001, 123, 5132-5133.
6. (a) Comins, D. L.; Zhang, Y.-M.; Joseph, S. P. Org. Lett. 1999, 1, 657-60.
7. (b) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719-28.
8. (a) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-517.
9. (b) Garner, P.; Kaniskan, H. Ü.; Hu, J.; Youngs, W. J.; Panzner, M. Org. Lett. 2006, 8, 3647-50.
10. (c) Hanselmann, R.; Zhou, J.; Ma., P.; Confalone, P. N. J. Org. Chem. 2003, 68, 8739-41.
11. (d) Ibrahem, I.; Rios, R.; Vesely, J.; Córdova, A. Tetrahedron Lett. 2007, 48, 6252-57.
12. (e) Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168-70.
13. Takasu, K.; Maiti, S.; Ihara, M. Heterocycles 2003, 59, 51-55.
14. Metal-catalyzed: (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-60.
15. (b) Taylor, M. S.; Zalatan, D.; Lerchner, A. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 1313-17.
16. (c) Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393-97Organocatalyzed:
17. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635-38.
18. (e) Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328-29.
19. (f) Ibrahem, I.; Rios, R.; Vesely, J.; Zhao, G.-L.; Córdova, A. Chem. Commun. 2007, 849-51.
20. (g) Vesely, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.; Cordova, A. Tetrahedron Lett. 2007, 48, 2193.
21. (h) Dinér, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983-87.
22. (i) Li, H.; Wang, J.; Xie, H.; Zu, L.; Jiang, W.; Duesler, E. N.; Wang, W. Org. Lett. 2007, 9, 965-68.
23. (j) Wang, J.; Zu, L.; Xie, H.; Wang, W. Synthesis 2007, 2576-80.
24. (k) Gerasyuto, A. I.; Hsung, R. P.; Sydorenko, N.; Slafer, B. J. Org. Chem. 2007, 70, 4248-56.
25. (l) Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065-92.
26. Fustero, S.; Jiménez, D.; Moscardó, J.; Catalán, S.; del Pozo, C. Org. Lett. 2007, 9, 5283-86.
27. Marigo, M; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794-97.
28. One explanation for this observation could be the difference in the dielectric constants between chloroform (4.8) and 1,2-dichloroethane (10.3).
29. Vehlow, K.; Gessler, S.; Blechert, S. Angew. Chem. Int.Ed. 2007, 46, 8082-85.
30. Walborsky, H. M.; Topolski, M.; Hamdouchi, C.; Pankowski, J. J. Org. Chem. 1992, 57, 6188-91.
31. Toshimitsu, A.; Terao, K.; Uemura, S. J. Org. Chem. 1986, 51, 1724-29.
32. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735-66.
33. Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130-31.
34. (a) Danishefsky, S.; Taniyama, E.; Webb, R. R., II Tetrahedron Lett. 1983, 24, 11-14.
35. (b) Webb, R. R., II; Danishefsky, S Tetrahedron Lett. 1983, 24, 1357-60.
36. (c) Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, 1747-1749.
37. (a) Marshall, W. D.; Nguyen, T. T.; MacLean, D. B.; Spenser, I. D. Can. J. Chem. 1975, 53, 41-50.
38. (b) Murahashi, S.; Kodera, Y.; Hosomi, T. Tetrahedron Lett. 1988, 29, 5949-52.
39. Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253-65.
40. (a) Tanret, C. Compt. Rend. 1878, 86, 1270.
41. (b) Tanret, C. Compt. Rend. 1880, 90, 695.
42. (a) Menzies, R. C.; Robinson, R. J. Chem. Soc., Trans. 1924, 125, 2163-8.
43. (b) King, J. A.; Hofmann, V.; McMillan, F. H. J. Org. Chem. 1951, 16, 1100-10.
44. (c) Galinovsky, F.; Vogl, O.; Weiser, R. Monatsch. Chem. 1952, 83, 114-22.
45. (d) Miller, F. M. J. Am. Chem. Soc. 1953, 75, 4849-50.
46. (e) Wibaut, J. P.; Hirschel, M. I. Recl. Trav. Chim. Pays-Bas 1956, 75, 225-36.
47. (f) Bowman, R. E.; Evans, D. D. J. Chem. Soc. 1956, 2553-55.
48. (g) Kuwata, S. Bull. Chem. Soc. Jpn. 1960, 33, 1672-8.
49. Gilman, R. E.; Marion, L. Bull. Soc. Chim. Fr. 1961, 1993-5.
50. (a) Beyerman, H. C.; Maat, L. Recl. Trav. Chim. Pays-Bas 1963, 82, 1033-39.
51. (b) Beyerman, H. C.; Maat, L. Recl. Trav. Chim. Pays-Bas 1965, 84, 385-88.
52. (c) Beyerman, H. C.; Maat, L.; van Veen, A.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1965, 84, 1367-79.
53. (a) Tanret, G. Bull. Soc. Chim. Fr. 1920, 27, 612-24.
54. (b) Wibaut, J. P.; Beets, M. G. J. Recl. Trav. Chim. Pays-Bas 1940, 59, 653-58.
55. (c) (d) Quick, J.; Oterson, R. Synthesis 1976, 745-46.
56. (e) Louis, C.; Mill, S.; Mancuso, V.; Hootele, C. Can. J. Chem. 1994, 72, 1347-50.
57. (f) Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047-54.
58. (a) Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047-54.
59. (b) Galinovsky, F.; Bianchetti, F.; Vogel, O. Monatsch. Chem. 1953, 84, 1221.
60. Synthesis and Medicinal Applications: (a) Wakabayashi, T.; Watanabe, K.; Kato, Y. Synth. Commun. 1977, 7, 239-44.
61. (b) Cardillo, G.; Gerntilucci, L.; Qasem, A. R.; Sgarzi, F.; Spampinato, S. J. Med. Chem. 2002, 45, 2571-78.
62. (c) Pousset, C.; Callens, R.; Marinetti, A.; Larcheveque, M. Synlett 2004, 2766-70.
63. (d) Zhang, Y. J.; Park, J. H.; Lee, S. Tetrahedron: Asymm. 2004, 15, 2209-12.
64. (e) Fülep, G. H.; Hoesl, C. E.; Höfner, G.; Wanner, K. T. Eur. J. Med. Chem. 2006, 41, 809-24
65. Organocatalysis: (f) Terakado, D.; Takano, M.; Oriyama, T. Chem. Lett. 2005, 34, 962-963.
66. (g) Limbach, M. Tetrahedron Lett. 2006, 47, 3843-47.