Cooperative catalysis approach to intramolecular hydroacylation

Journal of Organic Chemistry

Volumn 77, Issue 14, 2012, Pages 5884-5893

  Beletskiy, Evgeny V ^a   Sudheer, Ch ^a,b   Douglas, Christopher J ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF WISCONSIN EAU CLAIRE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATING GROUPS; COOPERATIVE CATALYSIS; DECARBONYLATIONS; HYDROACYLATION; INTRAMOLECULAR HYDROACYLATION; SEVEN-MEMBERED RINGS; SIX-MEMBERED RINGS; SUBSTRATE DESIGN;

ALDEHYDES; CHELATION; KETONES; OLEFINS; ORGANIC COMPOUNDS;

CATALYSIS;

(LEVO) 7 METHYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 2 FLUORO 7 METHYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 2 METHOXY 7 METHYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 2,7 DIMETHYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 7 [[(TERT BUTYLDIMETHYLSILYL) OXY] METHYL] 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 7 ETHYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 7 METHYL 2 (TRIFLUOROMETHYL) 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; 7 PHENYL 6,7,8,9 TETRAHYDRO 5H BENZO [7] ANNULEN 5 ONE; ALDEHYDE; ALKENE; KETONE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBONYLATION; CATALYSIS; CHELATION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROACYLATION;

EID: 84864057644     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300779q     Document Type: Article

References (71)

1. González-Rodríguez, C.; Willis, M. C. Pure Appl. Chem. 2011, 83, 577
2. Willis, M. C. Chem. Rev. 2010, 110, 725
3. Fu, G. C. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: New York, 2005; pp 79-91.
4. Tanaka, M.; Sakai, K.; Suemune, H. Curr. Org. Chem. 2003, 7, 353
5. Bosnich, B. Acc. Chem. Res. 1998, 31, 667
6. Marcé, P.; Díaz, Y.; Matheu, M. I.; Castillón, S. Org. Lett. 2008, 10, 4735
7. Kundu, K.; McCullagh, J. V.; Morehead, A. T. J. Am. Chem. Soc. 2005, 127, 16042
8. Cyclobutanones also formed: Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078
9. Tanaka, M.; Imai, M.; Fujio, M.; Sakamoto, E.; Takahashi, M.; Eto-Kato, Y.; Wu, X.-M.; Funakoshi, K.; Sakai, K.; Suemune, H. J. Org. Chem. 2000, 65, 5806
10. Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589
11. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821
12. Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron 1991, 47, 4879
13. Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190
14. Lochnow, C. F.; Miller, R. G. J. Am. Chem. Soc. 1976, 98, 1281
15. Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287
16. Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932
17. Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077
18. Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tily, T. A. Tetrahedron Lett. 2002, 43, 7031
19. Shibata, Y.; Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552
20. Tanaka, K.; Shibata, Y.; Suda, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 1215
21. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120
22. Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem., Int. Ed. 2006, 45, 6885
23. Oonishi, Y.; Mori, M.; Sato, Y. Synthesis 2007, 2323
24. Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218
25. Aloise, A. D.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 12610
26. Oonishi, Y.; Hosotani, A.; Sato, Y. J. Am. Chem. Soc. 2011, 133, 10386
27. Tanaka, K.; Hojo, D.; Shoji, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 2059
28. Tanaka, K.; Hagiwara, Y.; Hirano, M. Angew. Chem., Int. Ed. 2006, 45, 2734
29. Tanaka, K.; Hagiwara, Y.; Noguchi, K. Angew. Chem., Int. Ed. 2005, 44, 7260
30. Tanaka, K.; Fu, G. C. Org. Lett. 2002, 4, 933
31. Murphy, S. K.; Coulter, M. M.; Dong, V. M. Chem. Sci. 2012, 3, 355
32. Murphy, S. K.; Petrone, D. A.; Coulter, M. M.; Dong, V. M. Org. Lett. 2011, 13, 6216
33. Zhang, H.-J.; Bolm, C. Org. Lett. 2011, 13, 2900
34. Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330
35. Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354
36. Stemmler, R. T.; Bolm, C. Adv. Synth. Catal. 2007, 349, 1185
37. Imai, M.; Tanaka, M.; Nagumo, S.; Kawa-rara, N.; Suemune, H. J. Org. Chem. 2007, 72, 2543
38. Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Najumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144
39. Aldehydes containing a chelating sulfide: Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232
40. Tsuji, J.; Ohno, K. Tetrahedron Lett. 1965, 6, 3969
41. Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489
42. Park, Y. J.; Par, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
43. Vautravers, N. R.; Regent, D. D.; Breit, B. Chem. Commun. 2011, 47, 6635
44. Willis, M. C.; Sapmaz, S. Chem. Commun. 2001, 2558
45. Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070
46. Jun, C.-H.; Hong, J.-B. Org. Lett. 1999, 1, 887
47. Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200
48. Roy, A. H.; Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 2007, 129, 2082
49. Lenges, C. P.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 6965
50. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450
51. Compound 2g was reportedly prepared by an alternative synthesis, but our spectroscopic data did not match those provided in this preparation: Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316
52. Personal communication with Prof. Fillion, April 11th, 2011 and May 26th, 2011.
53. Piel, I.; Steinmetz, M.; Hirano, K.; Frölich, R.; Grimme, S.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 4983
54. Norman, R. O. C.; Coxon, J. M. Principles of Organic Synthesis, 3 rd ed.; CRC Press: Boca Raton, FL, 1993, p 67. From a synthesis standpoint, seven-membered rings are often prepared by ring expansion of six-membered rings. For a review, see
55. Kantorowski, E. J.; Kurth, M. J. Tetrahedron 2000, 56, 4317
56. Hyatt, I. F. D.; Anderson, H. K.; Morehead, A. T.; Sargent, A. L. Organometallics 2008, 27, 135 and references therein
57. Joe, C. L.; Tan, K. L. J. Org. Chem. 2011, 76, 7590
58. Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757
59. Van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1990, 90
60. Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412
61. Watson, I. D. G.; Ritter, S.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 2056
62. Conditions for these alkylations were adapted from the following: Bailey, W. F.; Wachter-Jurcsak, N. M.; Pineau, M. R.; Ovaska, T. V.; Warren, R. R.; Lewis, C. E. J. Org. Chem. 1996, 61, 8216
63. Prepared by allylic bromination of 2-phenylpropene according to Miyamura, H.; Akiyama, R.; Ishida, T.; Matsubara, R.; Takeuchi, M.; Kobayashi, S. Tetrahedron 2005, 61, 12177
64. Levine, S. R.; Krout, M. R.; Stolz, B. M. Org. Lett. 2009, 11, 289
65. Bonnaventure, I.; Charette, A. B. J. Org. Chem. 2008, 73, 6330
66. Previous preparation: Kirmse, W.; Höberger, G. J. Am. Chem. Soc. 1991, 113, 3925
67. Roy, H. N.; Rahman, A. F. M. M.; Islam, M. A. J. Chem. Res. 2003, 594
68. Zhang, T.; Huang, X.; Xue, J.; Sun, S. Tetrahedron Lett. 2009, 50, 1290
69. Adamczyk, M.; Watt, D.; Netzel, D. J. Org. Chem. 1984, 49, 4226
70. Gram-scale iodination of 2-aminopicoline (3) was previously described: Tao, L.; McLaughlin, L. W. J. Am. Chem. Soc. 2000, 122, 6512
71. Procedure adapted from Zhang, H.; Cai, Q; Ma, D. J. Org. Chem. 2005, 70, 5164