Enhanced rate and selectivity by carboxylate salt as a basic cocatalyst in chiral N-heterocyclic carbene-catalyzed asymmetric acylation of secondary alcohols

Journal of the American Chemical Society

Volumn 135, Issue 31, 2013, Pages 11485-11488

  Kuwano, Satoru ^a   Harada, Shingo ^a   Kang, Bubwoong ^a   Oriez, Raphaël ^a   Yamaoka, Yousuke ^a   Takasu, Kiyosei ^a   Yamada, Ken Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ACYLATION; CARBOXYLATE SALTS; CATALYST LOADINGS; DESYM-METRIZATION; ELECTRON-DEFICIENT; KINETIC RESOLUTION; REACTION CONDITIONS; SECONDARY ALCOHOLS;

ACYLATION; CARBOXYLATION; CATALYSIS; LOADING; ORGANIC COMPOUNDS;

CATALYST SELECTIVITY;

ALCOHOL DERIVATIVE; CARBENE; CARBOXYLIC ACID; CYCLOHEXENE DERIVATIVE; OSELTAMIVIR; SODIUM CHLORIDE;

ACYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 84881255290     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4055838     Document Type: Article

References (71)

1. Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570
2. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
3. Enders, D.; Henseler, A. Adv. Synth. Catal. 2009, 351, 1749
4. Lathrop, S. P.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 13628
5. Li, Y.; Shi, F.-Q.; He, Q.-L.; You, S.-L. Org. Lett. 2009, 11, 3182
6. DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872
7. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
8. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
9. Tam, S. W.; Jimenez, L.; Diederich, F. J. Am. Chem. Soc. 1992, 114, 1503
10. Miyashita, A.; Suzuki, Y.; Nagasaki, I.; Ishiguro, C.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1997, 45, 1254
11. Noonan, C.; Baragwanath, L.; Connon, S. J. Tetrahedron Lett. 2008, 49, 4003
12. Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Tetrahedron 2009, 65, 3102
13. Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126
14. Reynolds, N. T.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518
15. Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914
16. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583
17. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587
18. Grasa, G. A.; Güveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812
19. Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613
20. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
21. Wurz, R. P. Chem. Rev. 2007, 107, 5570
22. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430
23. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809
24. Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230
25. Oriyama, T.; Hori, Y.; Imai, K.; Sasaki, R. Tetrahedron Lett. 1996, 37, 8543
26. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169
27. Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492
28. Iwasaki, F.; Maki, T.; Nakashima, W.; Onomura, O.; Matsumura, Y. Org. Lett. 1999, 1, 969
29. Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638
30. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226
31. Mandai, H.; Murota, K.; Mitsudo, K.; Suga, S. Org. Lett. 2012, 14, 3486
32. Lee, S. Y.; Murphy, J. M.; Ukai, A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 15149
33. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769
34. Hanefeld, U. Org. Biomol. Chem. 2003, 1, 2405
35. Ghanem, A.; Aboul-Enein, H. Y. Tetrahedron: Asymmetry 2004, 15, 3331
36. De Sarkar, S.; Biswas, A.; Song, C. H.; Studer, A. Synthesis 2011, 1974
37. Iwahana, S.; Iida, H.; Yashima, E. Chem.-Eur. J. 2011, 17, 8009
38. Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770
39. Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347
40. Recently, kinetic resolution of 3-hydroxy-3-substituted oxindoles was reported. See: Lu, S.; Poh, S. B.; Siau, W.-Y.; Zhao, Y. Angew. Chem., Int. Ed. 2013, 52, 1731
41. Desymmetrization of meso -diols: Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Org. Lett. 2007, 9, 371
42. Kuwano, S.; Harada, S.; Oriez, R.; Yamada, K. Chem. Commun. 2012, 48, 145
43. Seemayer, R.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49 (no s calculated because of diacylation)
44. Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385 (2b, s = 7)
45. Matsumura, Y.; Maki, T.; Murakami, S.; Onomura, O. J. Am. Chem. Soc. 2003, 125, 2052 (2b, s = 14; 2c, s = 28)
46. Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325 (2b, s = 22; 2c, s = 21)
47. Mazet, C.; Roseblade, S.; Köhler, V.; Pfaltz, A. Org. Lett. 2006, 8, 1879 (2b, s = 21)
48. Müller, C. E.; Wanka, L.; Jewell, K.; Schreiner, P. R. Angew. Chem., Int. Ed. 2008, 47, 6180
49. Hrdina, R.; Müller, C. E.; Schreiner, P. R. Chem. Commun. 2010, 46, 2689
50. Hrdina, R.; Müller, C. E.; Wende, R. C.; Wanka, L.; Schreiner, P. R. Chem. Commun. 2012, 48, 2498 (2a, s = 11; 2b-d, s > 50)
51. Enzymatic resolution of related substrates: Tanaka, M.; Demizu, Y.; Nagano, M.; Hama, M.; Yoshida, Y.; Kurihara, M.; Suemune, H. J. Org. Chem. 2007, 72, 7750 and references therein
52. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249
53. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
54. 4-Nitrobenzoic acid, 3.41: de Bettencourt-Dias, A.; Viswanathan, S. Dalton Trans. 2006, 4093
55. Benzoic acid, 4.01: Vulpius, D.; Geipel, G.; Baraniak, L.; Bernhard, G. Spectrochim. Acta, Part A 2006, 63, 603
56. 4-Dimethylaminobenzoic acid, 4.92: Smiataczowa, K.; Wawrzynow, A.; Korewa, R. Pol. J. Chem. 1995, 69, 1306
57. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418
58. Takikawa, H.; Suzuki, K. Org. Lett. 2007, 9, 2713
59. Rovis, T. Chem. Lett. 2008, 37, 2
60. Liu, F.; Bugaut, X.; Schedler, M.; Fröhlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 12626
61. Hsieh, S.-Y.; Binanzer, M.; Kreituss, I.; Bode, J. W. Chem. Commun. 2012, 48, 8892
62. Asymmetric Organocatalysis 1 & 2; List, B.; Maruoka, K., Eds.; Science of Synthesis; Thieme: Stuttgart, Germany, 2011.
63. Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312
64. Bruice, T. C.; Kundu, N. G. J. Am. Chem. Soc. 1966, 88, 4097
65. Owen, T. C.; Richards, A. J. Am. Chem. Soc. 1987, 109, 2520
66. Yang, D.; Zuccarello, G.; Mattes, B. R. Macromolecules 2002, 35, 5304
67. Hibbert, F.; Hunte, K. P. P. J. Chem. Soc., Perkin Trans. 2 1983, 1895
68. Activation of electrophiles via protonation: Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466
69. Facilitation of rate-determining proton transfer of intermediates: DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 10402
70. Enzymatic: Maestro, A.; Astorga, C.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3153 (7b, 33% conv. after 6 days, s > 100)
71. Non-enzymatic: Reference 7h (N -acetyl analogues of 7b, s = 51; 7c, s = 17).