Concerted amidation of activated esters: Reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer

Journal of the American Chemical Society

Volumn 136, Issue 33, 2014, Pages 11783-11791

  Allen, Scott E ^a   Hsieh, Sheng Ying ^b   Gutierrez, Osvaldo ^a   Bode, Jeffrey W ^b   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; ESTERIFICATION; ESTERS; ORGANIC ACIDS; QUANTUM THEORY;

AMIDE BOND FORMATION; ELECTRONIC CONTROLS; KINETIC RESOLUTION; N-HETEROCYCLIC CARBENES; PEPTIDE COUPLING; QUANTUM-MECHANICAL STUDY; REACTION MECHANISM; SELECTIVITY FACTORS;

KINETICS;

AMIDE; AMINE; CARBENOID; ESTER DERIVATIVE; HETEROCYCLIC AMINE; HYDROXAMIC ACID; PEPTIDE; REAGENT; CARBENE; ESTER; HETEROCYCLIC COMPOUND; METHANE;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; ENANTIOMER; PROTON TRANSPORT; QUANTUM MECHANICS; REACTION ANALYSIS; STEREOSPECIFICITY; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS;

AMIDES; AMINES; CATALYSIS; ESTERS; HETEROCYCLIC COMPOUNDS; HYDROXAMIC ACIDS; KINETICS; METHANE; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 84906351447     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja505784w     Document Type: Article

References (57)

1. Walsh, P. W.; Kozlowski, M. C. Fundamentals of Asymmetric Catalysis; University Science Books: Sausalito, CA, 2009.
2. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
3. Wende, R. C.; Schreiner, P. R. Green Chem. 2012, 14, 1821
4. Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471
5. Larionov, E.; Mahesh, M.; Spivey, A. C.; Wei, Y.; Zipse, H. J. Am. Chem. Soc. 2012, 134, 9390
6. Li, X.; Liu, P.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2008, 130, 13836
7. Shinisha, C. B.; Sunoj, R. B. Org. Lett. 2009, 11, 3242
8. Sanan, T.; RajanBabu, T. V.; Hadad, C. M. J. Org. Chem. 2010, 75, 2369
9. Yang, X.; Bumbu, V. D.; Liu, P.; Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, W.; Jiang, X.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2012, 134, 17605
10. Binanzer, M.; Hsieh, S.-Y.; Bode, J. W. J. Am. Chem. Soc. 2011, 133, 19698
11. Hsieh, S.-Y.; Binanzer, M.; Kreituss, I.; Bode, J. W. Chem. Commun. 2012, 48, 8892-8894
12. Kreituss, I.; Murakami, Y.; Binanzer, M.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 10660
13. For a subsequent report of an enzymetic resolution of N-heterocycles, see: Ghisleri, D.; Green, A. P.; Pontini, M.; Willies, S. C.; Rowles, I.; Frank, A.; Gorgan, G.; Turner, N. J. J. Am. Chem. Soc. 2013, 135, 10863
14. Sorrell, T. N. Organic Chemistry, 2 nd Ed.; University Science Books: Sausolito, CA, 2006.
15. Sung, D. D.; Koo, I. S.; Yang, K.; Lee, I. Chem. Phys. Lett. 2006, 426, 280
16. Singleton, D. A.; Merrigan, S. R. J. Am. Chem. Soc. 2000, 122, 11035
17. Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018
18. Liu, X.-Q.; Jin, L.; Kim, C. K.; Xue, Y. J. Mol. Catal. A.: Chem. 2012, 355, 102
19. Hedstrom, L. Chem. Rev. 2002, 102, 4501
20. Oie, T.; Loew, G. H.; Burt, S. K.; Binkley, J. S.; MacElroy, R. D. J. Am. Chem. Soc. 1982, 104, 6169
21. Antonczak, S.; Ruiz-Lopez, M. F.; Rivail, J. L. J. Am. Chem. Soc. 1994, 116, 3912
22. Yang, W.; Drueckhammer, D. G. Org. Lett. 2000, 2, 4133
23. Yang, W.; Drueckhammer, D. G. J. Am. Chem. Soc. 2001, 123, 11004
24. Wang, L.-h.; Zipse, H. Liebigs Ann. Chem. 1996, 1501
25. Gandour, R. D. Tetrahedron Lett. 1974, 15, 295
26. Duan, X.; Schreiner, S. J. Am. Chem. Soc. 1992, 114, 5849
27. Rangelov, M. A.; Petrova, G. P.; Yomtova, V. M.; Vayssilov, G. N. J. Org. Chem. 2010, 75, 6782
28. Rangelov, M. A.; Petrova, G. P.; Yomtova, V. M.; Vayssilov, G. N. J. Mol. Graphics Modell. 2010, 29, 246
29. Rangelov, M. A.; Vayssilov, G. N.; Yomtova, V. M.; D, P. D. Org. Biomol. Chem. 2005, 3, 737
30. Bunnett, J. F.; Davis, G. T. J. Am. Chem. Soc. 1960, 82, 665
31. Ilieva, S.; Galabov, B.; Musaev, D. G.; Morokuma, K.; Schaefer, H. F. I. J. Org. Chem. 2003, 68, 1496
32. Ilieva, S.; Atanasov, Y.; Kalcheva, V.; Galabov, B. J. Mol. Struct.: THEOCHEM 2003, 633, 49
33. Galabov, B.; Atanasov, Y.; Ilieva, S.; Schaefer, H. F. I. J. Phys. Chem. A 2005, 109, 11470
34. Galabov, B.; Ilieva, S.; Hadjieva, B.; Atanasov, Y.; Schaefer, H. F. I. J. Phys. Chem. A 2008, 112, 6700
35. Díaz, N.; Suárez, D.; Sordo, T. L.; Méndez, R.; Villacorta, J. M. Eur. J. Org. Chem. 2003, 4161
36. Xia, X.; Zhang, C.; Xue, Y.; Kim, C. K.; Yan, G. J. Chem. Theory Comput. 2008, 4, 1643
37. Rony, P. R. J. Am. Chem. Soc. 1969, 91, 6090
38. Fischer, C. B.; Steininger, H.; Stephenson, D. S.; Zipse, H. J. Phys. Org. Chem. 2005, 18, 901
39. Petrova, T.; Okovytyy, S.; Gorb, L.; Leszczynski, J. J. Phys. Chem. A 2008, 112, 5224
40. Jin, L.; Wu, Y.; Kim, C. K.; Xue, Y. J. Mol. Struct.: THEOCHEM 2010, 942, 137
41. M06-2X/6-311+G(d,p) solvated single point calculations using B3LYP geometries are more effective than B3LYP alone in estimating absolute reaction barriers, see: Krenske, E. H.; Agopcan, S.; Aviyente, V.; Houk, K. N.; Johnson, B. A.; Holmes, A. B. J. Am. Chem. Soc. 2012, 134, 12010
42. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397
43. Carpino, L. A.; Imazumi, H.; Foxman, B. M.; Vela, M. J.; Henklein, P.; El-Faham, A.; Klose, J.; Bienert, M. Org. Lett. 2000, 2, 2253
44. The selectivity factor was calculated using enthalpy because the overall entropies of all the transition states are similar and enthalpies are known to be less prone to error than free energies: Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Çelebi-ölçüm, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042
45. Anet, F. A. L.; Yavari, I. J. Am. Chem. Soc. 1977, 99, 2794-2796
46. Erdogdu, Y.; GüllüogÌlu, M. T. Spectrochim. Acta, Part A 2009, 74, 162
47. Kaminski, G. A.; Friesner, R. A.; Tirado-Rives, J.; Jorgensen, W. L. J. Phys. Chem. B 2001, 105, 6474
48. MacroModel, version 9.9; Schrödinger, LLC, New York, NY, 2012.
49. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
50. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
51. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200
52. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724
53. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265
54. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
55. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuj, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; J. A. Montgomery, J.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
57. Fukui, K. Acc. Chem. Res. 1981, 14, 363