Catalytic asymmetric transfer hydrogenation of α-ketoesters with hantzsch esters

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5653-5655

  Yang, Jung Woon ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; COPPER; DRUG DERIVATIVE; ESTER; KETONE; NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CATALYSIS; CHEMISTRY; MOLECULAR MIMICRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOL DEHYDROGENASE; CATALYSIS; COPPER; ESTERS; KETONES; MOLECULAR MIMICRY; NAD; STEREOISOMERISM;

EID: 33845993240     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0624373     Document Type: Article

References (80)

1. (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vols. I-III.
2. (b) Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
3. (c) Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinhein, Germany, 1997.
4. (a) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X.-J.; Kabalka, G. W. Tetrahedron Lett. 1998, 39, 5501.
5. For reviews, see: (b) Singh, V. K. Synthesis 1992, 605.
6. (c) Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384.
7. (a) Maitra, U.; Mathivanan, P. Tetrahedron: Asymmetry 1994, 5, 1171.
8. (b) Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993.
9. (c) Solodin, I.; Goldberg, Y.; Zelcans, G.; Lukevics, E. J. Chem. Soc., Chem. Commun. 1990, 1321.
10. (a) Wang, C.-J.; Sun, X.; Zhang, X. Synlett 2006, 1169.
11. (b) Sun, Y.; Wan, X.; Wang, J.; Meng, Q.; Zhang, H.; Jiang, L.; Zhang, Z. Org. Lett. 2005, 7, 5425.
12. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029 and references cited therein.
13. (d) Jones, M. D.; Raja, R.; Thomas, J. M.; Johnson, B. F. G.; Lewis, D. W.; Rouzaud, J.; Harris, K. D. M. Angew. Chem., Int. Ed. 2003, 42, 4326.
14. (e) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolo, F. J. Org. Chem. 2000, 65, 2043.
15. (f) Blaser, H.-U.; Jalett, H.-P.; Spindler, F. J. Mol. Catal. A: Chem. 1996, 107, 85.
16. (g) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705.
17. (h) Mashima, K.; Kusano, K.-h.; Sato, N.; Matsumura, Y.-i.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
18. (a) Zuo, X.; Liu, H.; Guo, D.; Yang, X. Tetrahedron 1999, 55, 7787.
19. (b) For a review, see: Blaser, H.-U.; Jalett, H.-P.; Müller, M.; Studer, M. Catal. Today 1997, 37, 441.
20. (c) Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473.
21. (a) Zhu, D.; Yang, Y.; Hua, L. J. Org. Chem. 2006, 71, 4202.
22. (b) Kanomata, N.; Nakata, T. J. Am. Chem. Soc. 2000, 122, 4563.
23. (c) Kanomata, N.; Nakata, T. Angew. Chem., Int. Ed. 1997, 36, 1207.
24. (d) Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841.
25. (e) Meyers, A. I.; Brown, J. D. J. Am. Chem. Soc. 1987, 109, 3155.
26. (f) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1981, 103, 4613.
27. (g) de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759.
28. (h) Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036.
29. (i) Ohnishi, Y.; Kagarni, M.; Ohno, A. J. Am. Chem. Soc. 1975, 97, 4766.
30. (a) Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
31. (b) Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870.
32. (a) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
33. (b) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
34. (c) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
35. (d) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108.
36. (e) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424.
37. (f) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
38. (g) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660.
39. For the use of the Hantzsch ester as the reductant in asymmetric catalysis by other groups, see: (h) Tuttle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662.
40. (i) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
41. (j) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
42. (k) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
43. (l) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
44. (a) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559.
45. (b) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895.
46. (c) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599.
47. (a) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMilian, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
48. (b) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
49. (a) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50.
50. (b) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125.
51. (a) Yang, D.; Yang, M.; Zhu, N.-Y. Org. Lett. 2003, 5, 3749.
52. (b) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824.
53. (a) Halland, N.; Velgaard, T.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 5067.
54. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865.
55. (c) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.
56. (a) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420.
57. (b) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
58. (a) Jensen, K. B.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160.
59. (b) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517.
60. (a) Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875.
61. (b) Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843.
62. (a) Marigo, M.; Kjærsgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem.-Eur. J. 2003, 9, 2359.
63. (b) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995.
64. Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325.
65. (a) Körner, M.; Hiersemann, M. Synlett 2006, 121.
66. (b) For a review, see: Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.
67. Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806.
68. For a catalytic asymmetric addition reaction to α-ketoester and a similar substrate with alternative metal complexes, see: (a) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
69. (b) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 6532.
70. (c) Blay, G.; Fernández, I.; Marco-Aleixandre, A.; Pedro, J. R. Org. Lett. 2006, 8, 1287.
71. (d) Wieland, L. C.; Deng, H.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 15453.
72. (e) Harb, W.; Ruiz-Lopez, M. F.; Coutrot, F.; Grison, C.; Coutrot, P. J. Am. Chem. Soc, 2004, 126, 6996.
73. (f) Funabashi, K.; Jachmann, M.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2003, 42, 5489.
74. (g) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668.
75. For a single example of a chiral Sn-(pybox) complex-catalyzed reduction of an α-ketoester with polymethyl-hydrosiloxane (PMHS), see: Lawrence, N. J.; Bushell, S. M. Tetrahedron Lett. 2000, 41, 4507.
76. (a) Filho, M. V.; Stillger, T.; Müller, M.; Liese, A.; Wandrey, C. Angew. Chem., Int. Ed. 2003, 42, 2993.
77. (b) Lo, H. C.; Fish, R. H. Angew. Chem., Int. Ed. 2002, 41, 478.
78. 3. The organic layer was dried (MgSCM), filtered, and concentrated in vacuo to yield the crude product as an off-white solid. Purification by column chromatography (15% EtOAc/ hexanes) gave the pure product as a white solid (92.2 mg, 89%), identical in all respects to previously described tert-butyl (S)-mandelate 2d. [α]D +90.7 (c 1.0, MeOH) [[α]D +97.4 (c 1.0, MeOH), for >99:1 er].
79. For reviews of bisoxazoline-Lewis acid complexes as catalysts, see: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
80. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605.