Enantioselective mannich reactions with the practical proline mimetic N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2246-2249

  Yang, Hua ^a   Carter, Rich G ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-METHYL-TETRAHYDROFURAN; ALTERNATIVE METHODS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE; MANNICH REACTIONS; NON-POLAR SOLVENTS;

AMINES; AMINO ACIDS; CATALYSIS; ORGANIC ACIDS;

CATALYSTS;

2 METHYL TETRAHYDROFURAN; AMIDE; BETA AMINO ACID; N (4 DODECYLPHENYLSULFONYL) 2 PYRROLIDINECARBOXAMIDE; PROLINE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

CATALYSIS; KETONES; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PROLINE; PYRROLIDINES; STEREOISOMERISM; SULFONES;

EID: 64249148782     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8027938     Document Type: Article

References (46)

1. Martin, S. F. Acc. Chem. Res. 2002, 35, 895-904.
2. Enantioselective Synthesis of Beta-Amino Acids; Juaristi, E., Soloshonok, V. A., Eds.; Wiley-VCH: Hoboken, NJ, 2005.
3. For recent reviews, see: (a) Melchiorre, P.: Marigo, M.: Carlone, A.; Bartolim, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171.
4. (b) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4338-4360.
5. (c) Longbottom, D. A.; Franckevicius, V.; Kumarn, S.; Oelke, A. J.; Wascholowski, V.; Ley, S. V. Aldrichim. Acta 2008, 41, 3-11.
6. (d) Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29-41.
7. (e) Mukherjee. S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569.
8. (f) Ting, A.; Schaus, S. E. Em: J. Org. Chem. 2007, 2007, 5797-5815.
9. For select examples, see: (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002,124, 827-833.
10. (b) Notz, W.; Tanaka, F.; Watanabe, S.-i.; Chowdari. N. S.; Turner. J. M.; Thayumanavan, R.; Barbas, C. F., III. Org. Chem. 2003, 68, 9624-9634.
11. (c) Notz, W.; Watanabe, S.; Chowdari, N. S.; Zhong. G.; Betancort, J. M.; Tanaka, F.; Barbas, C. F., III. Adv. Synth. Catal. 2004, 346, 1131-1140.
12. (d) Westermann, B.; Neuhaus, C. Angew. Chem., Int. Ed. 2005, 44, 4077-4079.
13. (e) Hayashi, Y.; Urushima, T.; Tsuboi, W.; Shoji, M.: Nat. Protocols 2007, 2, 113-117.
14. (f) Yang, J. W.; Chandler, C.; Stadler, M.; Kampen. D.; List. B. Nature 2008, 452, 453-455.
15. For a computational investigation in proline-catalyzed Mannich reactions, see: (a) Parasuk, W.; Parasuk, V. J. Org. Chem. 2008, 73, 9388-9392.
16. (b) Allemann, C.; Gordillo. R.; demente, F. R.; Cheong. P. H.-Y.; Houk, K. N. Acc Chem. Res. 2004, 37, 558-569.
17. One impressive exception is a series of glycolate imine-derived Mannich reactions performed in dioxane: Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867.
18. (a) Cobb, A. J. A.; Shaw, D. M.: Longbottom. D. A.; Gold, J. B.: Ley, S. V. Org. Biomol Chem. 2005, 3, 84-96.
19. (b) Franzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jørgensen, K. A. J. Am, Chem. Soc. 2005. 127, 18296-18304.
20. (c) Enders, D.; Grondai. C.: Vrettou, M. Synthesis 2006, 3597-3604.
21. (d) Ibrahem, L.; Córdova, A. Chem, Commun. 2006, 17601762.
22. (e) Hayashi, Y.; Urshima, T.; Aratake, S.; Okano, T.; Obi, K. Org. Lett. 2008, 10, 21-24.
23. (f) Kano, T.; Hato, Y.; Yamamoto, A.; Maruoka, K. Tetrahedron 2008. 64, 1197-1203.
24. (g) Pouliquen. M.; Blanchet. J.; Lasne, M. C.; Rouden, J. Org. Lett. 2008, 10, 1029-1032.
25. (h) Hayashi, Y.; Okano, T.; Itoh, T.; Urushima, T.; Ishikawa, H.; Uchimaru, T. Angew. Chem., Int. Ed. 2008, 47, 9053-9058.
26. Yang, H.; Carter, R. G. Org. Lett 2008, 10, 4649-4652.
27. Water effects in oreanocatalyzed aldol reactions: (a) Nyberg. A. L.; Usano, A.; Pihko, P. M. Synlett 2004, 1891-1896.
28. (b) Pihko, P. M.; Laurikainen, K. M.; Usano, A.; Nyberg, A. L.; Kaavi, J. A. Tetrahedron 2006, 62, 317-328.
29. (c) Hayashi, Y.; Sumiya, T.; Takahashi. J.; Gotoh, H.; Urushima, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 958-961.
30. (d) Aratake, S.; Itoh, T.; Okano, T.; Nagae, N.; Sumiya, T.; Shoji, M.; Hayashi, Y. Chem. Eur. J. 2007, 13, 1024610256. Effects of water on organocatalyzed Mannich reactions:
31. (e) Itoh, T.; Yokoya, M.; Mivauchi, K.; Nagata, K.: Ohsawa. A. Org. Lett. 2003, 5, 4301-4304.
32. (f) See also ref 4c.
33. Secondary amine catalysts: (a) Córdova, A.; Barbas, C. F. Tetrahedron Lett. 2002, 43, 7749-7752.
34. (b) Kano, T.; Yamaguchi, Y.; Tokuda. O., Maruoka, K J. Am. Chem, Soc. 2005, 127, 16408-16409.
35. (c) Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am, Chem. Soc 2006, 128, 1040-1041.
36. (d) Zhang. H.: Mifsud, M.: Tanaka. F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 9630-9631.
37. (e) Kano, T.; Hato, Y.; Maruoka, K. Tetrahedron Lett. 2006, 47, 8467-8469.
38. (f) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc 2007, 129, 288-289.
39. (g) Dziedzic, P.; Córdova, A. Tetrahedron: Asymmetry 2007, 18, 1033-1037.
40. (h) Zhang, H.; Mitsumori, S.; Utsumi, N.; Imai, M.; Garcia-Delgado, N.; Mifsud, M.; Albertshofer, K.: Cheong, P. H.-Y.: Houk, K. N.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2008, 130, 875-886.
41. (i) Zhang, H.; Ramasastry, S. S. V.; Tanaka, F.; Barbas, C. F., III. Adv. Synth. Catal. 2008, 350, 791-796.
42. (j) Gianelli, C.; Sambri, L.; Carlone, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8700-8702. For a review of primary amine organocatalysts, see:
43. (k) Xu, L.-W.; Lu, Y. Org. Biomol. Chem, 2008, 6, 2047-2053.
44. (a) Yang, J. W.; Stadler, M.; List, B. Angew. Chem. Int. Ed. 2007, 46, 609-611.
45. (b) Vesley, J.; Rios, R.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2007, 48, 421-425.
46. Wenzel, A. G.; Jacobsen. E. N. J. Am. Chem. Soc. 2002, 124, 1296412965.