Origin of stereocontrol in guanidine-bisurea bifunctional organocatalyst that promotes α-hydroxylation of tetralone-derived β-ketoesters: Asymmetric synthesis of β- And γ-substituted tetralone derivatives via organocatalytic oxidative kinetic resolution

Journal of the American Chemical Society

Volumn 137, Issue 5, 2015, Pages 1909-1915

  Odagi, Minami ^a   Furukori, Kota ^a   Yamamoto, Yoshiharu ^a   Sato, Makoto ^b   Iida, Keisuke ^a   Yamanaka, Masahiro ^b   Nagasawa, Kazuo ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DESIGN FOR TESTABILITY; ENANTIOSELECTIVITY; HYDROXYLATION; KINETICS; SELECTIVE CATALYTIC REDUCTION;

ASYMMETRIC SYNTHESIS; CUMENE HYDROPEROXIDE; ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; NATURAL PRODUCTS; POTENTIAL UTILITY; SELECTIVITY FACTORS; TRANSITION STATE MODELING;

SYNTHESIS (CHEMICAL);

CUMENE HYDROPEROXIDE; ESTER DERIVATIVE; GUANIDINE; LINOXEPIN; NATURAL PRODUCT; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE; BETA-TETRALONE; ESTER; LIGNAN; UREA;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HYDROXYLATION; KINETICS; ORGANOCATALYST; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CATALYSIS; ESTERS; GUANIDINE; HYDROXYLATION; KINETICS; LIGNANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; STEREOISOMERISM; TETRALONES; UREA;

EID: 84922780754     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511149y     Document Type: Article

References (77)

1. Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Eur. J. Org. Chem. 2006, 2894-2897
2. Takada, K.; Nagasawa, K. Adv. Synth. Catal. 2009, 351, 345-347
3. Takada, K.; Tanaka, S.; Nagasawa, K. Synlett 2009, 1643-1646
4. Sohtome, Y.; Shin, B.; Horitsugi, N.; Takagi, R.; Noguchi, K.; Nagasawa, K. Angew. Chem., Int. Ed. 2010, 49, 7299-7303
5. Sohtome, Y.; Tanaka, S.; Takada, K.; Yamaguchi, T.; Noguchi, K.; Nagasawa, K. Angew. Chem., Int. Ed. 2010, 49, 9254-9257
6. Sohtome, Y.; Shin, B.; Horitsugi, N.; Noguchi, K.; Nagsawa, K. Chem.-Asian J. 2011, 6, 2463-2470
7. Sohtome, Y.; Yamaguchi, T.; Shin, B.; Nagasawa, K. Chem. Lett. 2011, 40, 843-845
8. Odagi, M.; Furukori, K.; Watanabe, T.; Nagasawa, K. Chem.-Eur. J. 2013, 19, 16740-16745
9. Cheong, P. H-Y.; Legault, C. Y.; Um, J. M.; Çelebi-Ölçüm, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042-5137
10. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
11. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
12. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364-382
13. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986, and references cited therein.
14. 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.; Nakatsuji, 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.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; 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, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2013.
15. Hamza, A.; Schubert, G.; Soós, T.; Pápai, I. J. Am. Chem. Soc. 2006, 128, 13151-13160
16. Zhu, R.; Zhang, D.; Wu, J.; Liu, C. Tetrahedron: Asymmetry 2006, 17, 1611-1616
17. Zhang, D.; Wang, G.; Zhu, R. Tetrahedron: Asymmetry 2008, 19, 568-576
18. Chen, D.; Lu, N.; Zhang, G.; Mi, S. Tetrahedron: Asymmetry 2009, 20, 1365-1368
19. Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15358-15374
20. Almas-i, D.; Alonso, D. A.; Gómez-Bengoa, E.; Nájera, C. J. Org. Chem. 2009, 74, 6163-6168
21. Uyeda, C.; Rötheli, A. R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 9753-9756
22. Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 5062-5075
23. Zhu, J.-L.; Zhang, Y.; Liu, C.; Zheng, A.-M.; Wang, W. J. Org. Chem. 2012, 77, 9813-9825
24. Shubina, T. E.; Freund, M.; Schenker, S.; Clark, T.; Tsogoeva, S. B. Beilstein J. Org. Chem. 2012, 8, 1485-1498
25. Gómez-Torres, E.; Alonso, D. A.; Gómez-Bengoa, E.; Nájera, C. Eur. J. Org. Chem. 2013, 1434-1440
26. Azuma, T.; Kobayashi, Y.; Sakata, K.; Sasamori, T.; Tokitoh, N.; Takemoto, Y. J. Org. Chem. 2014, 79, 1805-1817
27. Kótai, B.; Kardos, G.; Hamza, A.; Farkas, V.; Pápai, I.; Soós, T. Chem.-Eur. J. 2014, 20, 5631-5639
28. Morokuma, K.; Kitaura, K. I Chemical Applications of Atomic and Molecular Electrostatic Potentials; Politzer, P.; Truhlar, D. G., Eds.; Plenum: New York, 1981.
29. Ess, D. N.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646-10647
30. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187-10198
31. Lam, Y.-H.; Cheong, P. H.-Y.; Blasco Mata, J. M.; Stanway, S. J.; Gouverneur, V. R.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 1947-1957
32. Paton, R. S.; Kim, S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. Angew. Chem., Int. Ed. 2011, 50, 10366-10368
33. Green, A. G.; Liu, P.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575-4583
34. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806
35. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295-7306
36. Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682-4698
37. Oka, M.; Kamei, H.; Hamagishi, Y.; Tomita, K.; Miyaki, T.; Konishi, M.; Oki, T. J. Antibiot. 1990, 43, 967-976
38. Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79-85
39. Laurent, D.; Guella, G.; Mancini, I.; Roquebert, M. F.; Farinole, F.; Pietra, F. Tetrahedrone 2002, 58, 9163-9167
40. Wang, K. W.; Mao, J. S.; Tai, Y. P.; Pan, Y. J. Bioorg. Med. Chem. Lett. 2006, 16, 2274-2277
41. Cueva, J. P.; Godoy, A. G.; Juncosa, J. I.; Vidi, P. A.; Lill, M. A.; Watts, V. J.; Nichols, D. E. J. Med. Chem. 2011, 54, 5508-5521
42. Devkota, K. P.; Covell, D.; Ransom, T.; McMahon, J. B.; Beutler, J. A. J. Nat. Prod. 2013, 76, 710-714
43. Izawa, M.; Kimata, S.; Maeda, A.; Kawasaki, T.; Hayakawa, Y. J. Antibiot. 2014, 67, 159-162
44. Fieser, L. F.; Dunn, J. T. J. Am. Chem. Soc. 1936, 58, 572-575
45. Engman, L. Tetrahedron Lett. 1985, 26, 6385-6388
46. Engman, L. J. Org. Chem. 1988, 53, 4031-4037
47. Vargas, A. C.; Martin, I. P.; Sire, B. Q.; Zard, S. Z. Org. Biomol. Chem. 2004, 2, 3018-3025
48. Cui, L. Q.; Dong, Z. L.; Liu, K.; Zhang, C. Org. Lett. 2011, 13, 6488-6491
49. Yang, T. F.; Wang, K. Y.; Li, H. W.; Tseng, Y. C.; Lien, T. C. Tetrahedron Lett. 2012, 53, 585-588
50. Kasai, M.; Ziffer, H.; Silverton, J. V. Can. J. Chem. 1985, 63, 1287-1291
51. Caro, Y.; Torrado, M. A.; Masaguer, C. F.; Raviña, E.; Padin, F.; Brea, J.; Loza, M. A. I. Bioorg. Med. Chem. lett. 2004, 14, 585-589
52. Ros, A.; Magriz, A.; Dietrich, H.; Fernandez, R.; Alvarez, E.; Lassaletta, J. M. Org. Lett. 2006, 8, 127-130
53. Ding, Z.; Yang, J.; Wang, T.; Shen, Z.; Zhang, Y. Chem. Commun. 2009, 571-573
54. Genêt, J. P.; Pfister, X.; Vidal, V. R.; Pinel, C.; Laffitte, J. A. Tetrahedron Lett. 1994, 35, 4559-4562
55. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 1081-1082
56. Caro, Y.; Torrado, M. A.; Masaguer, C. F.; Raviña, E. Tetrahedron: Asymmetry 2003, 14, 3689-3696
57. Ros, A.; Magriz, A.; Dietrich, H.; Fernandez, R.; Alvarez, E.; Lassaletta, J. M. Org. Lett. 2006, 8, 127-130
58. Ding, Z.; Yang, J.; Wang, T.; Shen, Z.; Zhang, Y. Chem. Commun. 2009, 571-573
59. Manoni, F.; Connon, S. J. Angew. Chem., Int. Ed. 2014, 53, 2628-2632
60. Nicolaou, K. C.; Gray, D. L.; Tae, J. J. Am. Chem. Soc. 2004, 126, 613-627
61. Ting, C. P.; Maimone, T. J. Angew. Chem., Int. Ed. 2014, 53, 3115-3119
62. Yang, F. Z.; Trost, M. K.; Fristad, W. E. Tetrahedron Lett. 1987, 28, 1493-1496
63. Esteban, G.; López-Sánchez, M. A.; Martínez, M.; Plumet, J. Tetrahedron 1998, 54, 197-212
64. Pita, B.; Masaguer, C. F.; Ravina, E. Tetrahedron Lett. 2002, 43, 7929-7932
65. Cui, D. M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007-4010
66. Prakash, G. K. S.; Yan, P.; Torok, B.; Olah, G. A. Catal. Lett. 2003, 87, 109-112
67. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204-10205
68. Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316-1327
69. White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251
70. Elford, T. G.; Nave, S.; Sonawane, R. P.; Aggarwal, V. K. J. Am. Chem. Soc. 2011, 133, 16798-16801
71. Reddel, J. C.; Lutz, K. E.; Diagne, A. B.; Thomson, R. J. Angew. Chem., Int. Ed. 2014, 53, 1395-1398
72. Absolute configurations were determined by X-ray crystallography. See supporting information for details. CCDC 1018477 (p -BrBz 6k) and 1018478 (p -BrBz 6q) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
73. Schmidt, T. J.; Vossing, S.; Klaes, M.; Grimme, S. Planta Med. 2007, 73, 1574-1580
74. Tietze, L. F.; Duefert, S. C.; Clerc, J.; Bischoff, M.; Maass, C.; Stalke, D. Angew. Chem., Int. Ed. 2013, 52, 3191-3194
75. Weinstabl, H.; Suhartono, M.; Qureshi, Z.; Lautens, M. Angew. Chem., Int. Ed. 2013, 52, 5305-5308
76. Qureshi, Z.; Weinstabl, H.; Suhartono, M.; Liu, H.; Thesmar, P.; Lautens, M. Eur. J. Org. Chem. 2014, 4053-4069
77. Tietze, L. F.; Clerc, J.; Biller, S.; Duefert, S. C.; Bischoff, M. Chem.-Eur. J. 2014, 20, 17119-17124