Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17605-17612

  Yang, Xing ^a   Bumbu, Valentina D ^a   Liu, Peng ^b   Li, Ximin ^a   Jiang, Hui ^a   Uffman, Eric W ^a   Guo, Lei ^a   Zhang, Wei ^a   Jiang, Xuntian ^a   Houk, K N ^b   Birman, Vladimir B ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL RECOGNITION; DENSITY FUNCTIONAL THEORY CALCULATIONS; ENANTIOSELECTIVE; ENZYMATIC ACYLATION; KINETIC RESOLUTION;

AMIDES; CATALYSTS; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY;

ACYLATION;

ALCOHOL DERIVATIVE; AMIDINE; AMINE; CATION; LACTAM; THIOLACTAM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY;

ACYLATION; AMIDINES; CATALYSIS; LACTAMS; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 84867833954     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306766n     Document Type: Article

References (82)

1. Phosphodiesterase inhibitor Rolipram (pyrrolidinone): Schwabe, U.; Miyake, M.; Ohga, Y.; Daly, J. W. Mol. Pharmacol. 1976, 12, 900
2. Antibiotic Linezolid (oxazolidin-2-one): Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673
3. Cholesterol-lowering drug Ezetimibe (β-lactam): Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973
4. Testero, S. A.; Fisher, J. F.; Mobashery, S. β-Lactam antibiotics. In Burgers Medicinal Chemistry, Drug Discovery and Development, 7 th ed.; Abraham, D. J.; Rotella, D. P., Eds.; Wiley: Hoboken, NJ, 2010; Vol. 7 (Antiinfectives), pp 259-404.
5. Evans, D. A. Aldrichimica Acta 1982, 15, 23
6. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997, 30, 3
7. Velázquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 1
8. Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604
9. Boeckman, R. K.; Boehmler, D. J.; Musselman, R. A. Org. Lett. 2001, 3, 3777
10. E.g., chiral dirhodium carboxamidates: Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
11. Imidazolidin-4-ones as chiral enolate equivalents: Seebach, D.; Sting, A, R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708 and references cited therein
12. Vince lactam (2-azabicyclo[2.2.1]hept-5-en-3-one) in the synthesis of pharmaceuticals: Singh, R.; Vince, R. Chem. Rev. 2012, 112, 4642 and references cited therein
13. Proteasome inhibitor Lactacystin: Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113
14. Proteasome inhibitor Salinosporamide A: Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355
15. Angiogenesis inhibitor Streptopyrrolidine: Shin, H. J.; Kim, T. S.; Lee, H.-S.; Park, J. Y.; Choi, I.-K.; Kwon, H. J. Phytochemistry 2008, 69, 2363
16. Cytokine modulator Cytoxazone (oxazolidin-2-one): Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.-i.; Kobayashi, K.; Osada, H. J. Org. Chem. 1999, 64, 1052
17. Tetramic acids (pyrrolidine-2,4-diones): Royles, B. J. L. Chem. Rev. 1995, 95, 1981
18. C-H insertion: Doyle, M. P.; Kalinin, A. V. Synlett 1995, 1075
19. Staudinger reaction: Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578
20. France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592
21. Kinugasa reaction: Shintani, R.; Fu, G. C. Angew. Chem., Int. Edit. 2003, 42, 4082
22. NHC-catalyzed annulation: He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418
23. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128 (26) 8418
24. Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378
25. Simal, C.; Lebl, T.; Slawin, A. M. Z.; Smith, A. D. Angew. Chem., Int. Edit. 2012, 51, 3653
26. rac- Imidazolidin-4-ones: Zehavi, U.; Ben-lshai, D. J. Org. Chem. 1961, 26, 1097
27. Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389
28. Ishibuchi, S.; Ikematsu, Y.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1991, 32, 3523
29. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598
30. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131
31. For a review of resolution methods, see: Faigl, F.; Fogassy, E.; Nógrádi, M.; Pálovics, E.; Schindler, J. Tetrahedron Asymm. 2008, 19, 519
32. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226
33. Birman, V. B.; Jiang, H. Org. Lett. 2005, 7, 3445
34. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351
35. Birman, V. B.; Li, X. Org. Lett. 2008, 10, 1115
36. Li, X.; Liu, P.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2008, 130, 13836
37. Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, Y.; Yang, X.; Birman, V. B. J. Org. Chem. 2012, 77, 1722 and references cited therein
38. Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536
39. Yang, X.; Bumbu, V. D.; Birman, V. B. Org. Lett. 2011, 13, 4755
40. Yang, X.; Lu, G.; Birman, V. B. Org. Lett. 2010, 12, 892
41. Yang, X.; Birman, V. B. Angew. Chem., Int. Ed. 2011, 50, 553
42. Yang, X.; Birman, V. B. Chem.-Eur. J. 2011, 17, 11296
43. Bumbu, V. D.; Birman, V. B. J. Am. Chem. Soc. 2011, 133, 13902
44. Liu, P.; Yang, X.; Birman, V. B.; Houk, K. N. Org. Lett. 2012, 14, 3288
45. Yang, X.; Liu, P.; Houk, K. N.; Birman, V. B. Angew. Chem., Int. Ed. 2012, 51, 9776
46. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249
47. For a recent review, see: Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471
48. For a review of enzymatic KR of amines: van Rantwijk, F.; Sheldon, R. A. Tetrahedron 2004, 60, 501
49. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
50. Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613
51. Spivey, A. C.; Arseniyadis, S. Top. Curr. Chem. 2010, 291, 233
52. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
53. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
54. Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234
55. Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264
56. De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060
57. Klauber, E. G.; De, C. K.; Shah, T. K.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 13624
58. Klauber, E. G.; Mittal, N.; Shah, T. K.; Seidel, D. Org. Lett. 2011, 13, 2464
59. De, C. K.; Seidel, D. J. Am. Chem. Soc. 2011, 133, 14538
60. Mittal, N.; Sun, D. X.; Seidel, D. Org. Lett. 2012, 14, 3084
61. Binanzer, M.; Hsieh, S. Y.; Bode, J. W. J. Am. Chem. Soc. 2011, 133, 19698
62. Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem., Int. Ed. 1998, 37, 2349
63. Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D. R. Tetrahedron Lett. 2000, 41, 2239
64. Arseniyadis, S.; Valleix, A.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2004, 43, 3314
65. Maezaki, N.; Furusawa, A.; Uchida, S.; Tanaka, T. Tetrahedron 2001, 57, 9309
66. Karnik, A. V.; Kamath, S. S. Tetrahedron Asymm. 2008, 19, 45
67. Ishizuka, T.; Kimura, K.; Ishibuchi, S.; Kunieda, T. Chem. Lett. 1992, 991
68. Hashimoto, N.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1998, 39, 6317
69. Jouglet, B.; Rousseau, G. Tetrahedron Lett. 1993, 34, 2307
70. Csomós, P.; Kanerva, L. T.; Bernáth, G.; Fülöp, F. Tetrahedron: Asymmetry 1996, 7, 1789
71. Evans, C.; McCague, R.; Roberts, S. M.; Sutherland, A. G.; Wisdom, R. J. Chem. Soc., Perkin Trans. 1 1991, 2276
72. Brieva, R.; Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068
73. Forró, E.; Paál, T.; Tasnádi, G.; Fülöp, F. Adv. Synth. Catal. 2006, 348, 917
74. For a review of available enzymatic methods, see: Forró, E.; Fülöp, F. Mini-Rev. Org. Chem. 2004, 1, 93
75. Fowler, B. S.; Mikochik, P. J.; Miller, S. J. J. Am. Chem. Soc. 2010, 132, 2870
76. Kano, S.; Yokomatsu, T.; Shibuya, S. Heterocycles 1990, 31, 1711
77. Ager, D. J.; Allen, D. R.; Schaad, D. R. Synthesis 1996, 1283
78. Hofle, G.; Steglich, W.; Vorbruggen, H. Angew. Chem., Int. Edit. Engl. 1978, 17, 569
79. Shiina, I.; Nakata, K.; Ono, K.; Sugimoto, M.; Sekiguchi, A. Chem.-Eur. J. 2010, 16, 167
80. 2O: Hansen, M. M.; Harkness, A. R.; Coffey, D. S.; Bordwell, F. G.; Zhao, Y. Tetrahedron Lett. 1995, 36, 8949
81. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
82. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157