Formal aromatic C-H insertion for stereoselective isoquinolinone synthesis and studies on mechanistic insights into the C-C bond formation

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6231-6236

  Park, Chan Pil ^a   Nagle, Advait ^b   Cheol, Hwan Yoon ^a   Chen, Chiliu ^b   Kyung, Woon Jung ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL BONDS; DEUTERIUM; RHODIUM; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; C-C BOND FORMATION; C-H INSERTION; CARBENOIDS; CHEMICAL EQUATIONS; DEUTERIUM KINETIC ISOTOPE EFFECT; DIASTEREO-SELECTIVITY; DIRHODIUM; ELECTRON-RICH AROMATICS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; ISOQUINOLINONES; SIX-MEMBERED RINGS; STEREO-SELECTIVE; SUBSTITUENT EFFECT;

AROMATIZATION;

AROMATIC COMPOUND; CARBENOID; CARBON; DEUTERIUM; ELECTROPHILE; HYDROGEN; ISOQUINOLINE; RHODIUM; DIAZOACETAMIDE; DIAZOACETIC ACID ETHYL ESTER; DIAZONIUM COMPOUND; ISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ELECTRON; MOLECULAR MECHANICS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; CATALYSIS; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; KINETICS; STEREOISOMERISM;

CARBON; CATALYSIS; DIAZONIUM COMPOUNDS; HYDROGEN; ISOQUINOLINES; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RHODIUM; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 70349111092     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9011255     Document Type: Article

References (72)

1. (a) Bentley, K. W. The Isoquinoline Alkaloids; Hardwood Academic: Amsterdam, The Netherlands, 1998; Vol.1.
2. (b) Bently, K. W. Nat. Prod. Rep. 2001, 18, 148.
3. (c) Michael, J. P. Nat. Prod. Rep. 2002, 19, 742.
4. (d) Hansch, C. P.; Sammes, G.; Taylor, J. B. Comprehensive Medicinal Chemistry; Pergamon Press: Oxford, UK, 1990.
5. (e) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
6. (a) Durola, F.; Sauvage, J. P.; Wenger, O. S. Chem. Commun. 2006, 171.
7. (b) Sweetman, B. A.; Müller-Bunz, H.; Guiry, P. J. Tetrahedron Lett. 2005, 46, 4643.
8. (a) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
9. (b) Asao, N.; Yudha, S. S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526.
10. (c) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
11. (d) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
12. (e) Rose, M. D.; Cassidy, M. P.; Rashatasakhon, P.; Padwa, A. J. Org. Chem. 2007, 72, 538. 21.
13. (f) Garcia, E.; Arrasate, S.; Lete, E.; Sotomayor, N. J. Org. Chem. 2005, 70, 10368.
14. (g) Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11752.
15. (h) Zhang, F.; Simpkins, N. S.; Wilson, C. Tetrahedron Lett. 2007, 48, 5942.
16. (i) Chaumonte, M.; Piccardi, R.; Baudoin, O. Angew. Chem., Int. Ed. 2009, 48, 179.
17. (a) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. 1994, 33, 1797.
18. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
19. (c) Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2004, 3773.
20. (d) Merlic, C. A.; Zechman, A. L. Synthesis 2003, 8, 1137.
21. (e) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley and Sons: New York, 1998.
22. (a) Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669.
23. (b) Tsutsui, H.; Yamaguchi, Y.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Tetrahedron: Asymmetry. 2003, 14, 817.
24. (c) Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1992, 1508.
25. (d) Candeias, N. R.; Gois, P. M. P.; Afonso, C. A. M. J. Org. Chem. 2006, 71, 5489.
26. (e) Anada, M.; Hashimoto, S. Tetrahedron Lett. 1998, 39, 79.
27. (f ) Padwa, A.; Weingarten, M. D. J. Org. Chem. 2000, 65, 3722.
28. (a) Merlic, C. A.; Zechman, A. L.; Miller, M. M. J. Am. Chem. Soc. 2001, 123, 11101.
29. (b) Wee, A. G. H.; Duncan, S. C. Tetrahedron Lett. 2002, 43, 6173.
30. (c) Kane, J. L.; Shea, K. M.; Crombie, A. L.; Danheiser, R. L. Org. Lett. 2001, 3, 1081.
31. (d) Doyle, M. P.; Protopopova, M. N.; Peterson, C. S.; Vitale, J. P.; Mckervey, M. A.; Garcia, C. F. J. Am. Chem. Soc. 1996, 118, 7865.
32. (e) Yang, M.; Webb, T. R.; Livant, P. J. Org. Chem. 2001, 66, 4945.
33. (f ) Sugimura, T.; Im, C. Y.; Sato, Y.; Okuyama, T. Tetrahedron 2007, 63, 4027.
34. Rishton, G. M.; Schwartz, M. A. Tetrahedron Lett. 1988, 29, 2643.
35. (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
36. (b) Wee, A. G. H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404.
37. (c) Moody, C. J.; Miah, S.; Slawin, A. M. Z.; Mansfield, D. J.; Richards, I. C. Tetrahedron 1998, 54, 9689.
38. (d) Prein, M.; Manley, P. J.; Padwa, A. Tetrahedron 1997, 53, 7777.
39. (e) Davies, H. M. L.; Jin, Q.; Ren, P.; Kovalenvsky, A. Y. J. Org. Chem. 2002, 67, 4165.
40. (f ) Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971.
41. (a) Yoon, C. H.; Jaworotko, M. J.; Moulton, B.; Jung, K. W. Org. Lett. 2001, 3, 3539.
42. (b) Yoon, C. H.; Flanigan, D. L.; Chong, B. D.; Jung, K. W. J. Org. Chem. 2002, 67, 6582.
43. (c) Yoon, C. H.; Nagle, A.; Chen, C. L.; Gandhi, D.; Jung, K. W. Org. Lett. 2003, 5, 2259.
44. (d) Flanigan, D. L.; Yoon, C. H.; Jung, K. W. Tetrahedron. Lett. 2005, 46, 143.
45. (e) Yoon, C. H.; Flanigan, D. L.; Yoo, K. S.; Jung, K. W. Eur. J. Org. Chem. 2007, 37.
46. (f) Jung, Y. C.; Yoon, C. H.; Turos, E.; Yoo, K. S.; Jung, K. W. J. Org. Chem. 2007, 72, 10114.
47. (a) Taber, D. F.; Ruckle, R. E. Jr. J. Am. Chem. Soc. 1986, 108, 7686.
48. (b) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
49. For the leading references to a comformational study of N-acyloxazolidines, see: (a) Porter, N. A.; Bruhnke, J. D.; Wu, W, X.; Rosenstein, I. J.; Breyer, R. A. J. Am. Chem. Soc. 1991, 113, 7788.
50. (b) Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8631.
51. For the leading references to other studies with α-diazo-α- phenylsulfonyl compounds see: (a) Wee, A. G. H.; Slobodian, J. J. Org. Chem. 1996, 61, 2897.
52. (b) Padwa, A.; Straub, C. S. Org. Lett. 1999, 1, 83.
53. (c) Moody, C. J.; Davies, M. J. J. Chem. Soc., Perkin Trans. 1 1991, 9.
54. (d) Monteiro, H. J. Tetrahedron Lett. 1987, 28, 3459.
55. (e) Takeda, H.; Nakada, M. Tetrahedron: Asymmetry 2006, 17, 2896.
56. For the leading references to other studies with α-diazo-α- alkoxyphosphoryl compounds see: (a) Davis, F. A.; Bowen, K. A.; Xu, H.; Velvadapu, V. Tetrahedron 2008, 64, 4174.
57. (b) Davis, F. A.; Zhang, J.; Qiu, H.; Wu, Y. Org. Lett. 2008, 10, 1433.
58. (c) Zhang, W.; Romo, D. J. Org. Chem. 2007, 72, 8939.
59. (d) Xu, C.; Zhang, Y.; Yuan, C. Eur. J. Org. Chem. 2004, 10, 2253.
60. Which is more commonly invoked for the activation of C-H bonds by highly electrophilic late transition metal systems. (a) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180.
61. (b) Zhou, C. X.; Larock, R. C. J. Org. Chem. 2006, 71, 3551.
62. Doyle, M. P.; Shanklin, M. S.; Pho, H. Q.; Mahapatro, S. N. J. Org. Chem. 1988, 53, 1017.
63. (a) Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1991, 32, 3755.
64. (b) Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299.
65. Although we confirmed the deuterated product 32 through crude NMR data, the transferred deuterium was lost after column chromatography (see the Supporting Information for NMR spectra). Therefore, the deuterated product 32 would be the kinetically favored one via the proposed transition state before H/D exchange or equilibration (e.g., silica column). Besides, we could not observe the other diastereomer during the reaction.
66. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 27, 5541.
67. (a) Griffin, G. W.; Horn, K. A. J. Am. Chem. Soc. 1987, 109, 4919.
68. (b) Kang, M. J.; Song, W. J.; Han, A. R.; Choi, Y. S.; Jang, H. G.; Nam, W. W. J. Org. Chem. 2007, 72, 6301.
69. Wang, F. M.; Wang, J.; Hengge, A. C.; Wu, W. Org. Lett. 2007, 9, 1663 and references cited therein.
70. Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
71. (a) Davies, H. M. L.; Smith, H. D.; Hu, B.; Klenzak, S. M.; Hegner, F. J. J. Org. Chem. 1992, 57, 6900.
72. (b) Davies, H. M. L.; Jung, Q. Org. Lett. 2004, 6, 1769.