Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6233-6244

  Wang, Xiao Na ^a   Winston Mcpherson, Gabrielle N ^a   Walton, Mary C ^a   Zhang, Yu ^a   Hsung, Richard P ^a   Dekorver, Kyle A ^b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b DOW AGROSCIENCES LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON NUCLEOPHILES; ELECTRON WITHDRAWING GROUP; IONIC INTERMEDIATES; PALLADIUM CATALYSIS; TANDEM CASCADE; THERMAL CONDITION; YNAMIDES;

CHEMICAL COMPOUNDS; SCAFFOLDS;

CATALYSIS;

AMPHOLYTE; CHEMICAL COMPOUND; CYCLOPENTENIMINE DERIVATIVE; N ALLYL YNAMIDE DERIVATIVE; NUCLEOPHILE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CLAISEN REARRANGEMENT; CYCLIZATION; ELECTRON; SYNTHESIS; TEMPERATURE;

AMIDES; AZA COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOPENTANES; IMINES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84879347058     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400960e     Document Type: Article

References (80)

1. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
2. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
3. Ackermann, L.; Potukuchi, H. K. Org. Biomol. Chem. 2010, 8, 4503
4. Domínguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430
5. Weding, N.; Hapke, M. Chem. Soc. Rev. 2011, 40, 4525
6. Madelaine, C.; Valerio, V.; Maulide, N. Chem.-Asian J. 2011, 6, 2224
7. Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379
8. Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 43, 973
9. Tracey, M. R.; Hsung, R. P.; Antoline, J. A.; Kurtz, K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Weinreb, S. M., Ed.; Georg Thieme Verlag KG: Stuttgart, Germany, 2005; Chapter 21.4.
10. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
11. Evano, G.; Jouvinb, K.; Coste, A. Synthesis 2013, 17
12. Jin, X.; Yamaguchi, K.; Mizuno, N. Chem. Lett. 2012, 41, 866
13. Jin, X.; Yamaguchi, K.; Mizuno, N. Chem. Commun. 2012, 48, 4974
14. Jouvin, K.; Heimburger, J.; Evano, G. Chem. Sci. 2012, 3, 756
15. Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G. Organometallics 2012, 31, 7933
16. Tong, X.; Ni, G.; Deng, X.; Xia, C. Synlett 2012, 23, 2497
17. Wang, M.-G.; Wu, J.; Shang, Z.-C. Synlett 2012, 23, 589
18. Laouiti, A.; Jouvin, K.; Bourdreux, F.; Rammah, M. M.; Rammah, M. B.; Evano, G. Synthesis 2012, 44, 1491
19. Yne-sulfoxyimines: Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F.-F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 3478
20. Yne-hydrazides Beveridge, R. E.; Batey, R. A. Org. Lett. 2012, 14, 540
21. Yne-imines: Laouiti, A.; Rammah, M. M.; Rammah, M. B.; Marrot, J.; Couty, F.; Evano, G. Org. Lett. 2012, 14, 6
22. Ynimides: Souto, J. A.; Becker, P.; Iglesias, á.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 15505
23. Ynimides: Sueda, T.; Oshima, A.; Teno, N. Org. Lett. 2011, 13, 3996
24. Ynimides: Sueda, T.; Kawada, A.; Urash, Y.; Teno, N. Org. Lett. 2013, 15, 1560
25. Diamino-acetylenes: Petrov, A. R.; Daniliuc, C. G.; Jones, P. G.; Tamm, M. Chem.-Eur. J. 2010, 16, 11804
26. Amidinyl-ynamides: Li, J.; Neuville, L. Org. Lett. 2013, 15, 1752
27. Karmakar, R.; Mamidipalli, P.; Yun, S. Y.; Lee, D. Org. Lett. 2013, 15, 1938
28. Brioche, J.; Meyer, C.; Cossy, J. Org. Lett. 2013, 15, 1626
29. Yun, S. Y.; Wang, K.-P.; Lee, N.-K.; Mamidipalli, P.; Lee, D. J. Am. Chem. Soc. 2013, 135, 4668
30. Heffernan, S. J.; Beddoes, J. M.; Mahon, M. F.; Hennessy, A. J.; Carbery, D. R. Chem. Commun. 2013, 49, 2314
31. Kong, Y.; Jiang, K.; Cao, J.; Fu, L.; Yu, L.; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Org. Lett. 2013, 15, 422
32. Yavari, I.; Nematpour, M.; Sodagar, E. Synlett 2013, 24, 161
33. Yavari, I.; Nematpour, M. Synlett 2013, 24, 165
34. Bhunia, S.; Chang, C.-J.; Liu, R.-S. Org. Lett. 2012, 14, 5522
35. Minko, Y.; Pasco, M.; Lercher, L.; Botoshansky, M.; Marek, I. Nature 2012, 490, 522
36. Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208
37. Cao, J.; Kong, Y.; Deng, Y.; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Org. Biomol. Chem. 2012, 10, 9556
38. Greenaway, R. L.; Campbell, C. D.; Chapman, H. A.; Anderson, E. A. Adv. Synth. Catal. 2012, 354, 3187
39. Jiang, Z.; Lu, P.; Wang, Y. Org. Lett. 2012, 14, 6266
40. Gati, W.; Rammah, M. M.; Rammah, M. B.; Evano, G. Beilstein J. Org. Chem. 2012, 8, 2214
41. Smith, D. L.; Chidipudi, S. R.; Goundry, W. R.; Lam, H. W. Org. Lett. 2012, 14, 4934
42. Heffernan, S. J.; Carbery, D. R. Tetrahedron Lett. 2012, 53, 5180
43. Castro, A. M. M. Chem. Rev. 2004, 104, 2939
44. Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43
45. Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847
46. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 827.
47. Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984.
48. Majumdar, K. C.; Bhayyacharyya, T.; Chattopadhyay, B.; Nandi, R. K. Synthesis 2009, 2117
49. Nubbemeyer, U. Top. Curr. Chem. 2005, 244, 149
50. Zhang, Y.; DeKorver, K. A.; Lohse, A. G.; Zhang, Y.-S.; Huang, J.; Hsung, R. P. Org. Lett. 2009, 11, 899
51. DeKorver, K. A.; Hsung, R. P.; Lohse, A. G.; Zhang, Y. Org. Lett. 2010, 12, 1840
52. DeKorver, K. A.; Johnson, W. L.; Zhang, Y.; Hsung, R. P.; Dai, H.; Deng, J.; Lohse, A. G.; Zhang, Y.-S. J. Org. Chem. 2011, 76, 5092
53. DeKorver, K. A.; North, T. D.; Hsung, R. P. Synlett 2010, 2397
54. DeKorver, K. A.; Walton, M. C.; North, T. D.; Hsung, R. P. Org. Lett. 2011, 13, 4862
55. DeKorver, K. A.; Hsung, R. P.; Song, W.-Z.; Wang, X.-N.; Walton, M. C. Org. Lett. 2012, 14, 3214
56. DeKorver, K. A.; Wang, X.-N.; Walton, M. C.; Hsung, R. P. Org. Lett. 2012, 14, 1768
57. Krow, G. R. Angew. Chem., Int. Ed. 1971, 10, 435
58. Gambaryan, N. P. Usp. Khim. 1976, 45, 1251
59. Dondoni, A. Heterocycles 1980, 14, 1547
60. Barker, M. W.; McHenry, W. E. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley-Interscience: Chichester, UK, 1980; Part 2, pp 701-720.
61. Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. 2000, 4, 293
62. Rodríguez, D.; Martínez-Esperón, M. F.; Castedo, L.; Saá, C. Synlett 2007, 12, 1963
63. For a review, see: Basavaiah, D.; Jaganmohan Rao, A.; Satyanarayana, T. Chem. Rev. 2003, 103, 811
64. For a related report, see: Whiting, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3157
65. Rautenstrauch, V. J. Org. Chem. 1984, 49, 950
66. For a leading reference on Rautenstrauch rearrangements, see: Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802
67. For a related imino carbocyclization, see: Hanessian, S.; Tremblay, M.; Marzi, M.; Del Valle, J. R. J. Org. Chem. 2005, 70, 5070
68. Sosa, J. R.; Tudjarian, A. A.; Minehan, T. G. Org. Lett. 2008, 10, 5091
69. Tudjarian, A. A.; Minehan, T. G. J. Org. Chem. 2011, 76, 3576
70. Giese, S.; Kastrup, L.; Stiens, D.; West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970
71. Giese, S.; West, F. G. Tetrahedron 2000, 56, 10221
72. Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747
73. Huang, J.; Leboeuf, D.; Frontier A, J. J. Am. Chem. Soc. 2011, 133, 6307
74. Johnson, W. S. Acc. Chem. Res. 1968, 1, 1
75. Johnson, W. S. Angew. Chem., Int. Ed. 1976, 15, 9
76. For a key account, see: Johnson, W. S.; Telfer, S. J.; Cheng, S.; Schubert, U. J. Am. Chem. Soc. 1987, 109, 2517
77. Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068
78. Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890
79. Stadler, P. A.; Eschenmoser, A.; Schinz, H.; Stork, G. Helv. Chim. Acta 1957, 40, 2191
80. Coppola, G. M; Prashad, M. Syn. Commun. 1993, 23, 535