O-monoacyltartaric acid catalyzed enantioselective conjugate addition of a boronic acid to dienones: Application to the synthesis of optically active cyclopentenones

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5172-5175

  Sugiura, Masaharu ^a   Kinoshita, Ryo ^a   Nakajima, Makoto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BORONIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; PROSTAGLANDIN A; TARTARIC ACID; TARTARIC ACID DERIVATIVE; TEI9826;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BORONIC ACIDS; CATALYSIS; CYCLOPENTANES; MOLECULAR STRUCTURE; PROSTAGLANDINS A, SYNTHETIC; STEREOISOMERISM; TARTRATES;

EID: 84907698158     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502526y     Document Type: Article

References (71)

1. Conard, C. R.; Dolliver, M. A. Organic Synthesis; Wiley: New York, 1943; Collect. Vol. II, pp 167-168.
2. Arnold, A.; Markert, M.; Mahrwald, R. Synthesis 2006, 1099-1102
3. Kobayashi, S.; Semba, T.; Takahashi, T.; Yoshida, S.; Dai, K.; Otani, T.; Saito, T. Tetrahedron 2009, 65, 920-933
4. Sharma, M. K.; Banwell, M. G.; Willis, A. C.; Rae, A. D. Chem. - Asian J. 2012, 7, 676-679
5. Yang, H.; Hong, Y.-T.; Kim, S. Org. Lett. 2007, 9, 2281-2284
6. Silvanus, A. C.; Groombridge, B. J.; Andrews, B. I.; Kociok-Köhn, G.; Carbery, D. R. J. Org. Chem. 2010, 75, 7491-7493
7. For preparation of this reagent, see: Corbel, B.; Medinger, L.; Haelters, J. P.; Sturtz, G. Synthesis 1985, 1048-1051
8. Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196
9. Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; and references cited therein.
10. Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236
11. Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362
12. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844
13. Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279-1300
14. Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796-2823
15. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824-2852
16. Šebesta, R.; Pizzuti, M. G.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2007, 349, 1931-1937
17. Sieber, J. D.; Liu, S.; Morken, J. P. J. Am. Chem. Soc. 2007, 129, 2214-2215
18. Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2008, 130, 4978-4983
19. Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 1576-1577
20. Nishimura, T.; Tokuji, S.; Sawano, T.; Hayashi, T. Org. Lett. 2009, 11, 3222-3225
21. Li, X.-m.; Wang, B.; Zhang, J.-m.; Yan, M. Org. Lett. 2011, 13, 374-377
22. Hu, Z.-P.; Lu, C.-L.; Wang, J.-J.; Chen, C.-X.; Yan, M. J. Org. Chem. 2011, 76, 3797-3804
23. Imbos, R.; Brilman, M. H. G.; Pineschi, M.; Feringa, B. L. Org. Lett. 1999, 1, 623-626
24. Jagt, R. B. C.; Imbos, R.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. Isr. J. Chem. 2002, 41, 221-230
25. van Summeren, R. P.; Reijmer, S. J. W.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2005, 1387-1389
26. Bulic, B.; Lücking, U.; Pfaltz, A. Synlett 2006, 1031-1034
27. Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552-2553
28. Liu, D.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 8160-8161
29. Takizawa, S.; Nguyen, T. M.-N.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423-5426
30. Rubush, D. M.; Morges, M. A.; Rose, B. J.; Thamm, D. H.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 13554-13557
31. Wu, W.; Li, X.; Huang, H.; Yuan, X.; Lu, J.; Zhu, K.; Ye, J. Angew. Chem., Int. Ed. 2013, 52, 1743-1747
32. Hara, S.; Hyuga, S.; Aoyama, M.; Sato, M.; Suzuki, A. Tetrahedron Lett. 1990, 31, 247-250
33. Hara, S.; Shudoh, H.; Ishimura, S.; Suzuki, A. Bull. Chem. Soc. Jpn. 1998, 71, 2403-2408
34. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2007, 129, 4908-4909
35. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2005, 127, 3244-3245
36. Turner, H. M.; Patel, J.; Niljianskul, N.; Chong, J. M. Org. Lett. 2011, 13, 5796-5799
37. Lee, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 15438-15439
38. Kim, S.-G. Tetrahedron Lett. 2008, 49, 6148-6151
39. Inokuma, T.; Takasu, K.; Sakaeda, T.; Takemoto, Y. Org. Lett. 2009, 11, 2425-2428
40. Lundy, B. J.; Jansone-Popova, S.; May, J. A. Org. Lett. 2011, 13, 4958-4961
41. Le, P. Q.; Nguyen, T. S.; May, J. A. Org. Lett. 2012, 14, 6104-6107
42. Akagawa, K.; Sugiyama, M.; Kudo, K. Org. Biomol. Chem. 2012, 10, 4839-4843
43. Roscales, S.; Csákÿ, A. G. Org. Lett. 2012, 14, 1187-1189
44. Roscales, S.; Rincón, á.; Buxaderas, E.; Csákÿ, A. G. Tetrahedron Lett. 2012, 53, 4721-4724
45. Roscales, S.; Ortega, V.; Csákÿ, A. G. J. Org. Chem. 2013, 78, 12825-12830
46. Sugiura, M.; Tokudomi, M.; Nakajima, M. Chem. Commun. 2010, 46, 7799-7800
47. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746-1787
48. Samojłowicz, C.; Bieniek, M.; Grela, K. Chem. Rev. 2009, 109, 3708-3742
49. Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 2007, 40, 45-52
50. Adv. Synth. Catal. 2007, 349, 1-268.(Olefin Metathesis Special Issue)
51. Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140
52. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1-3.
53. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
54. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
55. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036-2056
56. Iqbal, M.; Evans, P. Tetrahedron Lett. 2003, 44, 5741-5745
57. Schelwies, M.; Dübon, P.; Helmchen, G. Angew. Chem., Int. Ed. 2006, 45, 2466-2469
58. Dübon, P.; Schelwies, M.; Helmchen, G. Chem. - Eur. J. 2008, 14, 6722-6733
59. Żurawiński, R.; Mikina, M.; Mikołajczyk, M. Tetrahedron: Asymmetry 2010, 21, 2794-2799
60. Grimblat, N.; Sugiura, M.; Pellegrinet, S. C. J. Org. Chem. 2014, 79, 6754-6758
61. Paton, R. S.; Goodman, J. M.; Pellegrinet, S. C. J. Org. Chem. 2008, 73, 5078-5089
62. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784
63. Wrobleski, A.; Sahasrabudhe, K.; Aubé, J. J. Am. Chem. Soc. 2004, 126, 5475-5481
64. Davis, F. A.; Wu, Y. Org. Lett. 2004, 6, 1269-1272
65. Chandler, C. L.; Phillips, A. J. Org. Lett. 2005, 7, 3493-3495
66. Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589-1592
67. Miura, Y.; Hayashi, N.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2012, 134, 11995-11997
68. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
69. To the best of our knowledge, the addition of 1,6-heptadiene as an ethylene equivalent was reported by Fukuyama and co-workers for the first time (ref 27.). Collins and co-workers also described a positive effect with other olefin additives; see: Grandbois, A.; Collins, S. K. Chem. - Eur. J. 2008, 14, 9323-9329
70. Trost, B. M. Science 1991, 254, 1471-1477
71. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40-49