One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives

Synlett

Volumn , Issue 11, 2003, Pages 1651-1654

  Córdova, Armando ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Aldehydes; Asymmetric catalysis; Asymmetric synthesis; Imines; Mannich reactions

Indexed keywords

ALDEHYDE; AMINOALCOHOL; IMINE; PROLINE;

ARTICLE; CATALYSIS; ENANTIOMER; MANNICH REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 4243162724     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41423     Document Type: Article

References (52)

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7. For examples of alternative asymmetric synthesis of 1,3-amino alcohols, see: (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518. (b) Yamamoto, Y.; Kornatsu, T.; Maryama, K. J. Chem. Soc., Chem. Commun. 1985, 814. (c) Toujas, J.-L.; Toupet, L.; Vaultier, M. Tetrahedron 2000, 56, 2665. (d) Barluenga, J.; Fernandez-Marí, F.; Viado, A. L.; Aguilar, E.; Olano, B. J. Org. Chem. 1996, 61, 5659.
8. For examples of alternative asymmetric synthesis of 1,3-amino alcohols, see: (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518. (b) Yamamoto, Y.; Kornatsu, T.; Maryama, K. J. Chem. Soc., Chem. Commun. 1985, 814. (c) Toujas, J.-L.; Toupet, L.; Vaultier, M. Tetrahedron 2000, 56, 2665. (d) Barluenga, J.; Fernandez-Marí, F.; Viado, A. L.; Aguilar, E.; Olano, B. J. Org. Chem. 1996, 61, 5659.
9. For examples of alternative asymmetric synthesis of 1,3-amino alcohols, see: (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518. (b) Yamamoto, Y.; Kornatsu, T.; Maryama, K. J. Chem. Soc., Chem. Commun. 1985, 814. (c) Toujas, J.-L.; Toupet, L.; Vaultier, M. Tetrahedron 2000, 56, 2665. (d) Barluenga, J.; Fernandez-Marí, F.; Viado, A. L.; Aguilar, E.; Olano, B. J. Org. Chem. 1996, 61, 5659.
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11. For examples of alternative catalytic asymmetric synthesis of β-amino acid derivatives, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperese, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (c) Nelson, S.; Spencer, K. L. Angew. Chem. Int. Ed. 2000, 39, 1323. (d) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (e) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
12. For examples of alternative catalytic asymmetric synthesis of β-amino acid derivatives, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperese, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (c) Nelson, S.; Spencer, K. L. Angew. Chem. Int. Ed. 2000, 39, 1323. (d) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (e) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
13. For examples of alternative catalytic asymmetric synthesis of β-amino acid derivatives, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperese, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (c) Nelson, S.; Spencer, K. L. Angew. Chem. Int. Ed. 2000, 39, 1323. (d) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (e) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
14. For examples of alternative catalytic asymmetric synthesis of β-amino acid derivatives, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperese, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (c) Nelson, S.; Spencer, K. L. Angew. Chem. Int. Ed. 2000, 39, 1323. (d) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (e) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
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16. For review, see: (a) Arend, M.; Westerman, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (c) Denmark, S.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamomoto, H., Eds.; Springer: Berlin, 1999, 93.
17. For review, see: (a) Arend, M.; Westerman, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (c) Denmark, S.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamomoto, H., Eds.; Springer: Berlin, 1999, 93.
18. (a) Palomo, C.; Oiarbide, M.; Gonzales-Rego, M. C.; Sharma, A. K.; Garcia, J. M.; Landa, C.; Linden, A. Angew. Chem. Int. Ed. 2000, 39, 1063.
19. (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287.
20. (c) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
21. (d) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
22. For recent catalytic asymmetric examples, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (c) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. (d) Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem. Int. Ed. 2001, 40, 2271.
23. For recent catalytic asymmetric examples, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (c) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. (d) Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem. Int. Ed. 2001, 40, 2271.
24. For recent catalytic asymmetric examples, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (c) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. (d) Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem. Int. Ed. 2001, 40, 2271.
25. For recent catalytic asymmetric examples, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180. (b) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (c) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. (d) Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem. Int. Ed. 2001, 40, 2271.
26. (a) Córdova, A.; Notz, W.; Barbas, C. F. III J. Org. Chem. 2002, 67, 301.
27. (b) Córdova, A.; Notz, W.; Barbas, C. F. III Chem. Commun. 2002, 3024.
28. (c) Watanabe, S.-i.; Córdova, A.; Tanaka, F.; Barbas, C. F. III Org. Lett. 2002, 4, 4519.
29. (d) Córdova, A.; Barbas, C. F. III Tetrahedron Lett. 2003, 44, 1923.
30. For other L-proline catalyzed aldehyde addition reactions, see: (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Bøgevig, A.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
31. For other L-proline catalyzed aldehyde addition reactions, see: (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Bøgevig, A.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
32. For other L-proline catalyzed aldehyde addition reactions, see: (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Bøgevig, A.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
33. For other L-proline catalyzed aldehyde addition reactions, see: (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620. (b) Bøgevig, A.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
34. (a) Cørdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1866.
35. (b) Cørdova, A.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 7749.
36. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
37. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
38. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
39. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
40. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
41. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
42. There are reports of direct asymmetric Mannich reactions with unmodified ketones, see: (a) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew Chem. Int. Ed. 2001, 40, 2995. (c) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (d) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (e) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842. (f) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (g) Matsunaga, S.; Kumagai, N. ; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
43. We observed that Mannich product 1 was unstable and racemized if stored at room temperature or subjected to silica gel column chromatography. In addition, 1 is prone to epimerization that decreases the diastereomeric ratio.
44. 2O: 40% yield, dr>10:1, 99% ee; and at 4 °C: THF: 36% yield, dr>10:1, >99% ee; dioxane: 62% yield, dr>10:1, 99% ee.
45. 4 (316.1423).
46. 4 (372.2048968).
47. 4), concentrated, and purified by flash column chromatography (silica gel, mixtures of hexanes/EtOAc) to afford 2.
48. (a) NMR-data of the major diastereomer of PMP-deprotected 6 was identical to the previously reported syndiastereomer, see: Jaeger, V.; Buss, V. ; Schwab, W. Liebigs Arm. Chem. 1980, 122.
49. 13C NMR: δ = 12.0, 40.9, 59.1, 66.2, 126.9, 127.1, 128.2, 143.9.
50. (c) L-Proline derived 6 had the same retention time as (2S,3S)-6 that had been synthesized via known procedures, see: Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030.
51. R = 14.02 min.
52. 2 (271.172206).