Dynamic kinetic resolution: Asymmetrie transfer hydrogénation of α-alkyl-substituted β-ketoamides

Organic Letters

Volumn 12, Issue 3, 2010, Pages 512-515

  Limanto, John ^a   Krska, Shane W ^a   Dorner, Benjamin T ^a   Vazquez, Enrique ^a   Yoshikawa, Naoki ^a   Tan, Lushi ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BETA KETOAMIDE; BETA LACTAM; BETA-KETOAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HYDROGENATION; KINETICS; STEREOISOMERISM; SYNTHESIS;

AMIDES; BETA-LACTAMS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROGENATION; KINETICS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 75749105381     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902715d     Document Type: Article

References (49)

1. (a) Mártin-Matute, B.; Bäckvall, J.-E. Curr. Opin. Chem. Biol. 2007, 11, 116.
2. (b) Turner, N. J. Curr. Opin. Chem. Biol. 2004, 8, 114.
3. (c) Pellisier, H. Tetrahedron 2003, 59, 8291.
4. (d) Pamies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247.
5. (e) Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J.-E. Chem. Soc. Rev. 2001, 30, 321.
6. (f) Ohkuma, T.; Kitamura, M.; Noyori, R. Catalytic Asymmetrie Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; p 1.
7. (g) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
8. (a) Wu, X.; Xiao, J. Chem. Commun. 2007, 2449.
9. (b) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
10. (c) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
11. (d) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201.
12. (e) Everaere, K.; Mortreux, A.; Carpentier, J. F. Adv. Synth. Catal. 2003, 345, 67.
13. (f) Saluzzo, C.; Lemaire, M. Adv. Synth. Catal. 2002, 344, 915.
14. (g) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931.
15. (h) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
16. (i) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
17. (j) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
18. (k) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
19. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
20. For representative examples, see: (a) Makino, K.; Hiroki, Y.; Hamada, Y. J. Am. Chem. Soc. 2005, 127, 5784.
21. (b) Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem., Int. Ed. Engl. 2004, 43, 882.
22. (c) Lei, A.; Wu, S.; He, M.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 9685.
23. (d) Mordant, C.; Dunkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Eur. J. Org. Chem. 2004, 3017.
24. (e) Mordant, C.; Dunkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J. P. Chem. Commun. 2004, 1296.
25. (a) Ros, A.; Magriz, A.; Dietrich, H.; Lassaletta, J. M.; Fernández, R. Tetrahedron 2007, 63, 7532.
26. (b) Fernández, R.; Ros, A.; Magriz, A.; Dietrich, H.; Lassaletta, J. M. Tetrahedron 2007, 63, 6755.
27. (c) Alcock, N. J.; Mann, I.; Peach, P.; Wills, M. Tetrahedron: Asymmetry 2002, 13, 2485.
28. (d) Mohar, B.; Valleix, A.; Desmurs, J.-R.; Felemez, M.; Wagner, A.; Mioskowski, C. Chem. Commun. 2001, 2572.
29. For an example of enzymatic DKR-ATH of 2-oxocyclopentanecarboxamides, see: Quirós, M.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1999, 10, 473.
30. For reviews, see: (a) Knapp, S. Chem. Rev. 1995, 95, 1859.
31. (b) Ohfune, H. Acc. Chem. Res. 1992, 25, 360.
32. For representative examples, see: (a) Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988.
33. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
34. (c) Thiruvengadam, T. K.; Sudhakar, A., R.; Wu, G. Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K. G., Ed.; Marcel Dekker, Inc.: New York, NY, 1999; p 221.
35. (d) Déziel, R.; Malenfant, E. Bioorg. Med. Chem. Lett. 1998, 8, 1437.
36. (e) Clader, J. W.; Burnett, D. A.; Caplen, M. A.; Domalski, M. S.; Dugar, S.; Vaccaro, W.; Sher, R.; Browne, M. E.; Zhao, H.; Burrier, R. E.; Salisbury, B.; Davis, H. R. J. Med. Chem. 1996, 39, 3684.
37. (f) Wild, H.; Kant, J.; Walker, D. G.; Ojima, I.; Temansky, R. J.; Morin, J. M., Jr.; Georg, G. I.; Rabikumar, V. T. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
38. For examples of nonasymmetric, but diastereoselective, reduction of racemic a-substituted β-ketoamides, see: (a) Bartoli, G.; Bosco, M.; Marcantoni, E.; Melchiorre, P.; Rinaldi, S.; Sambri, L. Synlett 2004, 1, 73.
39. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Tetrahedron Lett. 2001, 42, 8811.
40. (c) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1985, 107, 8294.
41. See Supporting Information for the synthesis of this compound.
42. Evans, D. A.; Ennis, M. D.; Le, T. J. Am. Chem. Soc. 1984, 106, 1154.
43. For ease of discussion, the term "enantioselectivity" refers to the absolute configuration at carbon 2 and 3 of the syn-epimer 3a while ignoring the fixed stereocenter at the benzylic carbon labeled 6 [i.e., (2R,3R,6S) vs (2S,3S,6S)].
44. The absolute stereochemistry was confirmed by X-ray single-crystal structure (see Supporting Information). Additional information can be found at the Cambridge Crystallographic Data Centre (CCDC) with deposition code of CCDC 752316.
45. (a) Bose, A. K.; Manhas, M. S.; Sahu, D. P.; Hedge, V. R. Can. J. Chem. 1984, 2498.
46. (b) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F. J. Am. Chem. Soc. 1980, 102, 7026.
47. For phase transfer catalyzed cyclization of O-phosphorylated or O-benzoylated substrates, see ref.8c For a nonphase transfer promoted process, see: Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986,27, 3119.
48. While executing the mesylation at higher temperatures (>5 °C) resulted in partial chloride displacement leading to syn β-lactams, performing the cyclization under homogenous conditions (KOtBu/THF or LiHMDS/ THF) gave initially the trans-β-lactam 6, which during the course of the reaction equilibrated rapidly to a 4:1 mixture of trans:syn β-lactams.
49. 3Si: C, 50.57; H, 5.09; N, 1.97. Found: C, 50.72; H, 5.10; N, 1.86.