Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1H-isochromene derivatives through an intramolecular-cyclization/ enantioselective-reduction sequence

Angewandte Chemie - International Edition

Volumn 53, Issue 1, 2014, Pages 235-239

  Terada, Masahiro ^a   Li, Feng ^a   Toda, Yasunori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; cyclization; enantioselective reduction; isobenzopyrylium ions; silver salts

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; BIOLOGICALLY ACTIVE MOLECULES; ENANTIOSELECTIVE REDUCTION; HIGH ENANTIOSELECTIVITY; ISOCHROMENE DERIVATIVES; SILVER SALTS; SYNTHETIC UTILITY;

CATALYSIS; CATALYSTS; CYCLIZATION; KETONES; MOLECULES; OLEFINS; PHOSPHATES; STEREOCHEMISTRY;

ENANTIOSELECTIVITY;

EID: 84890941094     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307371     Document Type: Article

References (85)

1. E.-V. Kuznetsov, I.-V. Shcherbakova, A.-T. Balaban, Adv. Heterocycl. Chem. 1990, 50, 157-254
2. M. Nogradi, Sci. Synth. 2003, 14, 201-273
3. J. Santamaría, C. Valdés, Mod. Heterocycl. Chem. 2011, 3, 1631-1682; for selected examples, see
4. J. D. Tovar, T. M. Swager, J. Org. Chem. 1999, 64, 6499-6504
5. I. Prauda, J. Reiter, J. Heterocycl. Chem. 2001, 38, 199-204
6. I. Prauda, I. Kövesdi, P. Trinka, J. Reiter, J. Heterocycl. Chem. 2001, 38, 403-414
7. T. Suzuki, C. Okada, K. Arai, A. Awaji, T. Shimizu, K. Tanemura, T. Horaguchi, J. Heterocycl. Chem. 2001, 38, 1409-1418
8. W.-G. Wei, Z.-J. Yao, J. Org. Chem. 2005, 70, 4585-4590.
9. N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651
10. N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628-3630
11. Angew. Chem. Int. Ed. 2003, 42, 3504-3506
12. N. Asao, T. Nogami, S. Lee, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921-10925
13. J.-L. Zhu, A.-R. Germain, J. A. Porco, Jr., Angew. Chem. 2004, 116, 1259-1263
14. Angew. Chem. Int. Ed. 2004, 43, 1239-1243
15. J.-L. Zhu, N. P. Grigoriadis, J.-P. Lee, J. A. Porco, Jr., J. Am. Chem. Soc. 2005, 127, 9342-9343
16. N. Asao, K. Sato, Menggenbateer, Y. Yamamoto, J. Org. Chem. 2005, 70, 3682-3685
17. H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709-2716
18. S. Shin, A.-K. Gupta, C.-Y. Rhim, C.-H. Oh, Chem. Commun. 2005, 4429-4431
19. A.-B. Beeler, S. Su, C.-A. Singleton, J. A. Porco, Jr., J. Am. Chem. Soc. 2007, 129, 1413-1419
20. Y.-C. Hsu, C.-M. Ting, R.-S. Liu, J. Am. Chem. Soc. 2009, 131, 2090-2091.
21. J. Barluenga, H. Vázquez-Villa, A. Ballesteros, J.-M. González, J. Am. Chem. Soc. 2003, 125, 9028-9029
22. J. Barluenga, H. Vázquez-Villa, A. Ballesteros, J.-M. González, Org. Lett. 2003, 5, 4121-4123
23. D. Yue, N. Della Cà, R.-C. Larock, Org. Lett. 2004, 6, 1581-1584
24. J. Barluenga, H. Vázquez-Villa, I. Merino, A. Ballesteros, J. M. González, Chem. Eur. J. 2006, 12, 5790-5805
25. D. Yue, N. Della Cà, R. C. Larock, J. Org. Chem. 2006, 71, 3381-3388.
26. Z.-L. Hu, W.-J. Qian, S. Wang, S. Wang, Z.-J. Yao, Org. Lett. 2009, 11, 4676-4679
27. Z.-L. Hu, W.-J. Qian, S. Wang, S. Wang, Z.-J. Yao, J. Org. Chem. 2009, 74, 8787-8793.
28. G. Dyker, D. Hildebrandt, J. Org. Chem. 2005, 70, 6093-6096
29. K. Sato, N. Asao, Y. Yamamoto, J. Org. Chem. 2005, 70, 8977-8981
30. M. A. Marsini, K. M. Gowin, T. R. R. Pettus, Org. Lett. 2006, 8, 3481-3483
31. W.-J. Qian, W.-G. Wei, Y.-X. Zhang, Z.-J. Yao, J. Am. Chem. Soc. 2007, 129, 6400-6401
32. Y.-S. Yao, Z.-J. Yao, J. Org. Chem. 2008, 73, 5221-5225.
33. D. Hojo, K. Noguchi, K. Tanaka, Angew. Chem. 2009, 121, 8273-8276
34. Angew. Chem. Int. Ed. 2009, 48, 8129-8132
35. S. Handa, L.-M. Slaughter, Angew. Chem. 2012, 124, 2966-2969
36. Angew. Chem. Int. Ed. 2012, 51, 2912-2915; for a catalytic enantioselective reaction of 2-oxonium-1,3-dienes, see
37. K. Ishida, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2010, 132, 8842-8843.
38. F. Benfatti, E. Benedetto, P. G. Cozzi, Chem. Asian J. 2010, 5, 2047-2052
39. P. N. Moquist, T. Kodama, S. E. Schaus, Angew. Chem. 2010, 122, 7250-7254
40. Angew. Chem. Int. Ed. 2010, 49, 7096-7100
41. M. Rueping, C. M. R. Volla, I. Atodiresei, Org. Lett. 2012, 14, 4642-4645
42. C.-C. Hsiao, H.-H. Liao, E. Sugiono, I. Atodiresei, M. Rueping, Chem. Eur. J. 2013, 19, 9775-9779
43. M. Terada, T. Yamanaka, Y. Toda, Chem. Eur. J. 2013, 19, 13658-13662.
44. M. Terada, Y. Toda, Angew. Chem. 2012, 124, 2135-2139
45. II catalyst and a chiral Lewis acid catalyst, see
46. H. Suga, K. Inoue, S. Inoue, A. Kakehi, J. Am. Chem. Soc. 2002, 124, 14836-14937
47. H. Suga, K. Inoue, S. Inoue, A. Kakehi, M. Shiro, J. Org. Chem. 2005, 70, 47-56
48. H. Suga, T. Suzuki, K. Inoue, A. Kakehi, Tetrahedron 2006, 62, 9218-9225
49. H. Suga, S. Higuchi, M. Ohtsuka, D. Ishimoto, T. Arikawa, Y. Hashimoto, S. Misawa, T. Tsuchida, A. Kakehi, T. Baba, Tetrahedron 2010, 66, 3070-3089.
50. During the preparation of our manuscript, an enantioselective transformation of isobenzopyrylium ions was reported:, S.-Y. Yu, H. Zhang, Y. Gao, L. Mo, S. Wang, Z.-J. Yao, J. Am. Chem. Soc. 2013, 135, 11402-11407.
51. J. Lacour, D. Moraleda, Chem. Commun. 2009, 7073-7089
52. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614
53. M. Mahlau, B. List, Angew. Chem. 2013, 125, 540-556
54. Angew. Chem. Int. Ed. 2013, 52, 518-533
55. K. Brak, E. N. Jacobsen, Angew. Chem. 2013, 125, 558-588
56. Angew. Chem. Int. Ed. 2013, 52, 534-561; see also
57. A. Parra, S. Reboredo, A. M. M. Castro, J. Alemán, Org. Biomol. Chem. 2012, 10, 5001-5020.
58. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499
59. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337
60. M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027-7030
61. Angew. Chem. Int. Ed. 2007, 46, 6903-6906
62. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450-14451
63. S. Liao, B. List, Angew. Chem. 2010, 122, 638-641
64. Angew. Chem. Int. Ed. 2010, 49, 628-631
65. G. Jiang, R. Halder, Y. Fang, B. List, Angew. Chem. 2011, 123, 9926-9929
66. Angew. Chem. Int. Ed. 2011, 50, 9752-9755
67. V. Rauniyar, Z. J. Wang, H. E. Burks, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 8486-8489
68. J. R. Zbieg, E. Yamaguchi, E. L. McInturff, M. J. Krische, Science 2012, 336, 324-327
69. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615-3618
70. Z.-L. Tao, W.-Q. Zhang, D.-F. Chen, A. Adele, L.-Z. Gong, J. Am. Chem. Soc. 2013, 135, 9255-9258.
71. S.-L. You, Chem. Asian J. 2007, 2, 820-827
72. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852-865
73. C. Zheng, S.-L. You, Chem. Soc. Rev. 2012, 41, 2498-2518.
74. 3 and a chiral phosphoric acid, see:, K. Aikawa, M. Kojima, K. Mikami, Angew. Chem. 2009, 121, 6189-6193
75. Angew. Chem. Int. Ed. 2009, 48, 6073-6077.
76. R. Yanada, S. Obika, H. Kono, Y. Takemoto, Angew. Chem. 2006, 118, 3906-3909
77. Angew. Chem. Int. Ed. 2006, 45, 3822-3825
78. S. Obika, H. Kono, Y. Yasui, R. Yanada, Y. Takemoto, J. Org. Chem. 2007, 72, 4462-4468.
79. CCDC 954470 [(S)- 4 k ] 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.
80. S. Bhunia, K.-C. Wang, R.-S. Liu, Angew. Chem. 2008, 120, 5141-5144
81. Angew. Chem. Int. Ed. 2008, 47, 5063-5066.
82. B. Wünsch, M. Zott, G. Höfner, Arch. Pharm. 1992, 325, 733-739
83. B. Wünsch, M. Zott, G. Höfner, Arch. Pharm. 1993, 326, 823-830
84. R. Dupont, L. Jeanson, J.-F. Mouscadet, P. Cotelle, Bioorg. Med. Chem. Lett. 2001, 11, 3175-3178
85. C. Maurin, F. Bailly, P. Cortelle, Curr. Med. Chem. 2003, 10, 1795-1810.