Mukaiyama-Michael reactions with trans-2,5-diarylpyrrolidine catalysts: Enantioselectivity arises from attractive noncovalent interactions, not from steric hindrance

Chemistry - A European Journal

Volumn 20, Issue 20, 2014, Pages 5983-5993

  Kemppainen, Eeva K ^a   Sahoo, Gokarneswar ^a   Piisola, Antti ^a   Hamza, Andrea ^b   Kõtai, Bianka ^b   Pápai, Imre ^b   Pihko, Petri M ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

DFT calculations; enantioselectivity; noncovalent interactions; organocatalysis; transition states

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; IONS; REACTION KINETICS; STEREOSELECTIVITY;

C-C BOND FORMATION; DFT CALCULATION; ENANTIOSELECTIVE CATALYSIS; INTER-MOLECULAR FORCES; NON-COVALENT INTERACTION; ORGANOCATALYSIS; RELATIVE ENERGIES; TRANSITION STATE;

ENANTIOSELECTIVITY;

EID: 84900016345     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201304240     Document Type: Article

References (70)

1. P. J. Walsh, M. C. Kozlowski, Fundamentals of Asymmetric Catalysis, University Science Books, Sausalito, California, 2009; see the discussion on pp. 115-116.
2. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
3. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416
4. P. M. Pihko, I. Majander, A. Erkkilä, Top. Curr. Chem. 2009, 291, 29-75.
5. K. C. Harper, M. S. Sigman, J. Org. Chem. 2013, 78, 2813-2818.
6. Isolation and characterization:, T. Yasumoto, M. Murata, Y. Oshima, M. Sano, G. K. Matsumoto, J. Clardy, Tetrahedron 1985, 41, 1019-1025
7. K. Sasaki, J. L. C. Wright, T. Yasumoto, J. Org. Chem. 1998, 63, 2475. For the total synthesis of PTX4 and PTX8, see
8. D. A. Evans, H. A. Rajapakse, D. Stenkamp, Angew. Chem. 2002, 114, 4751
9. Angew. Chem. Int. Ed. 2002, 41, 4569
10. D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755
11. Angew. Chem. Int. Ed. 2002, 41, 4573. For a recent total synthesis of pectenotoxin-2, see
12. K. Fujiwara, Y. Suzuki, N. Koseki, Y.-i. Aki, Y. Kikuchi, S.-i. Murata, F. Yamamoto, M. Kawamura, T. Norikura, H. Matsue, A. Murai, R. Katoono, H. Kawai, T. Suzuki, Angew. Chem. Int. Ed. 2014, 53, 780. For a review covering all synthetic studies towards the pectenotoxins until the year 2006, see
13. R. Halim, M. A. Brimble, Org. Biomol. Chem. 2006, 4, 4048-4058. For synthetic studies published after this review, see
14. K. Fujiwara, Y. Aki, F. Yamamoto, M. Kawamura, M. Kobayashi, A. Okano, D. Awakura, S. Shiga, A. Murai, H. Kawai, T. Suzuki, Tetrahedron Lett. 2007, 48, 4523
15. R. V. Kolakowski, L. J. Williams, Tetrahedron Lett. 2007, 48, 4761
16. P. D. OConnor, C. K. Knight, D. Friedrich, X. Peng, L. A. Paquette, J. Org. Chem. 2007, 72, 1747
17. D. Vellucci, S. D. Rychnovsky, Org. Lett. 2007, 9, 711
18. S. D. Lotesta, Y. Hou, L. J. Williams, Org. Lett. 2007, 9, 869
19. A. M. Heapy, T. W. Wagner, M. A. Brimble, Synlett 2007, 2359
20. S. Carley, M. A. Brimble, Org. Lett. 2009, 11, 563
21. A. M. Heapy, M. A. Brimble, Tetrahedron 2010, 66, 5424
22. S. Joyasawal, S. D. Lotesta, N. G. Akhmedov, L. J. Williams, Org. Lett. 2010, 12, 988
23. G. Vassilikogiannakis, I. Alexopoulou, M. Tofi, T. Montagnon, Chem. Commun. 2011, 47, 259-261
24. D. P. Canterbury, G. C. Micalizio, Org. Lett. 2011, 13, 2384-2387
25. K. Fujiwara, Y. Suzuki, N. Koseki, S.-I. Murata, A. Murai, H. Kawai, T. Suzuki, Tetrahedron Lett. 2011, 52, 5589-5592
26. A. Kouridaki, T. Montagnon, M. Tofi, G. Vassilikogiannakis, Org. Lett. 2012, 14, 2374-2377
27. O. Kubo, D. P. Canterbury, G. C. Micalizio, Org. Lett. 2012, 14, 5748-5751
28. A. Kouridaki, T. Montagnon, D. Kalaitzakis, G. Vassilikogiannakis, Org. Biomol. Chem. 2013, 11, 537-541
29. T. J. Donohoe, R. M. Lipinski, Angew. Chem. Int. Ed. 2013, 52, 2491-2494.
30. E. K. Kemppainen, G. Sahoo, A. Valkonen, P. M. Pihko, Org. Lett. 2012, 14, 1086-1089. For previous work from this laboratory, see
31. P. M. Pihko, J. E. Aho, Org. Lett. 2004, 6, 3849-3852
32. J. E. Aho, E. Salomäki, K. Rissanen, P. M. Pihko, Org. Lett. 2008, 10, 4179-4182
33. H. Helmboldt, J. E. Aho, P. M. Pihko, Org. Lett. 2008, 10, 4183-4185
34. J. E. Aho, A. Piisola, K. S. Krishnan, P. M. Pihko, Eur. J. Org. Chem. 2011, 1682.
35. A. Erkkilä, P. M. Pihko, M.-R. Clarke, Adv. Synth. Catal. 2007, 349, 802-806
36. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227-10229; Cyclopropanations
37. V. Terrasson, A. van der Lee, R. M. de Figueiredo, J. M. Campagne, Chem. Eur. J. 2010, 16, 7875-7880; Cycloadditions
38. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505
39. A. Sakakura, K. Suzuki, K. Nakano, K. Ishihara, Org. Lett. 2006, 8, 2229-2232
40. A. Sakakura, K. Suzuki, K. Ishihara, Adv. Synth. Catal. 2006, 348, 2457-2465
41. K. Ishihara, K. Nakano, M. Akakura, Org. Lett. 2008, 10, 2893-2896
42. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2007, 129, 8930-8931
43. T. Kano, Y. Tanaka, K. Osawa, T. Yurino, K. Maruoka, Chem. Commun. 2009, 15, 1956-1958; Aziridinations
44. L. Deiana, P. Dziedzic, G.-L Zhao, J. Vesely, I. Ibrahem, R. Rios, J. Sun, A. Cõrdova, Chem. Eur. J. 2011, 17, 7904-7917.
45. N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790-4791.
46. S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192-1194.
47. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
48. Angew. Chem. Int. Ed. 2005, 44, 4212-4215
49. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807
50. Angew. Chem. Int. Ed. 2005, 44, 794-797.
51. M. Benohoud, A. Erkkilä, P. M. Pihko, Org. Synth. 2010, 87, 201-208.
52. The preference of "closed" transition structures in the C-C bond formation between the iminium ion and pyrrole has been noted previously, and it has been associated with electrostatic stabilization of the developing partial charge on the pyrrole by the iminium π-system. See:, R. Gordillo, J. Carter, K. N. Houk, Adv. Synth. Catal. 2004, 346, 1175.
53. P. H. Cheong, C. Y. Legault, J. M. Um, N. Çelebi- Ölçüm, K. N. Houk, Chem. Rev. 2011, 111, 5042
54. I. Pápai, in Science of Synthesis: Asymmetric Organocatalysis, Vol. 2 (Eds.:, B. List, K. Maruoka,), Thieme, Stuttgart, 2012, pp. 601-632.
55. J. B. Brazier, G. Evans, T. J. K. Gibbs, S. J. Coles, M. B. Hursthouse, J. A. Platts, N. C. O. Tomkinson, Org. Lett. 2009, 11, 133
56. R. Gordillo, K. N. Houk, J. Am. Chem. Soc. 2006, 128, 3543.
57. E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras- García, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498
58. J. Contreras-García, E. R. Johnson, S. Keinan, R. Chaudret, J. Piquemal, D. N. Beratan, W. Yang, J. Chem. Theory Comput. 2011, 7, 625.
59. RDG isosurface plots were visualized by the VMD program:, W. Humphrey, A. Dalke, K. Schulten, J. Molec. Graphics 1996, 14, 33.
60. -1 difference in the transition states). See:, J. L. Arbour, H. S. Rzepa, J. Contreras-Garcia, L. A. Adrio, E. M. Barreiro, K. K. M. Hii, Chem. Eur. J. 2012, 18, 11317.
61. J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615
62. J.-D. Chai, M. Head-Gordon, J. Chem. Phys. 2008, 128, 084106.
63. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650
64. A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639
65. T. Clark, J. Chandrasekhar, G. W. Spitznagel, P. v. R. Schleyer, J. Comput. Chem. 1983, 4, 294
66. M. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 80, 3265.
67. L. Goerigk, S. Grimme, Phys. Chem. Chem. Phys. 2011, 13, 6670.
68. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
69. J. Tomasi, B. Mennucci, E. Cancès, J. Mol. Struct. 1999, 464, 211.
70. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378.