Synthesis of substituted 6-imino-2-piperidinones by Rh-catalyzed [4+2] annulation of 4-alkynals with carbodiimides

Tetrahedron

Volumn 65, Issue 44, 2009, Pages 9008-9014

  Tanaka, Ken ^a   Mimura, Marina ^a   Hojo, Daiki ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANAMIDE; PIPERIDONE DERIVATIVE; RHODIUM; TRANSITION ELEMENT;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 70349320322     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.115     Document Type: Article

References (80)

1. For reviews of transition-metal-catalyzed cycloadditions, see:
2. Yet L. Chem. Rev. 100 (2000) 2963
3. Wender P.A., and Love J.A. Advances in Cycloaddition Vol. 5 (1999), JAI, Greenwich p 1
4. Mehta G., and Singh V. Chem. Rev. 99 (1999) 881
5. Ojima I., Tzamarioudaki M., Li Z., and Donovan R.J. Chem. Rev. 96 (1996) 635
6. Lautens M., Klute W., and Tam W. Chem. Rev. 96 (1996) 49
7. Schore N.E. Chem. Rev. 88 (1988) 1081
8. For a review of cycloadditions through five-membered acylmetal intermediates leading to six-membered carbonyl compounds, see:. Tanaka K. Chim. Oggi 24 (2006) 20
9. For a review of rhodium-catalyzed [4+2] cycloadditions, see:. Robinson J.E. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim 241
10. Reppe W., and Vetter H. Justus Liebigs Ann. Chem. 582 (1953) 133
11. Maruyama K., Shio T., and Yamamoto Y. Bull. Chem. Soc. Jpn. 52 (1979) 1877
12. Foust D.F., and Rausch M.D. J. Organomet. Chem. 239 (1982) 321
13. Cabrera A., Mondragón J., Torres F., and Gómez L.J. Rev. Soc. Quim. Mex. 27 (1983) 311
14. Liebeskind L.S., Baysdon S.L., and South M.S. J. Am. Chem. Soc. 102 (1980) 7397
15. Baysdon S.L., and Liebeskind L.S. Organometallics 1 (1982) 771
16. South M.S., and Liebeskind L.S. J. Org. Chem. 47 (1982) 3815
17. Liebeskind L.S., and Baysdon S.L. Tetrahedron Lett. 25 (1984) 1747
18. South M.S., and Liebeskind L.S. J. Am. Chem. Soc. 106 (1984) 4181
19. Liebeskind L.S., Leeds J.P., Baysdon S.L., and Iyer S. J. Am. Chem. Soc. 106 (1984) 6451
20. Liebeskind L.S., Baysdon S.L., South M.S., Iyer S., and Leeds J.P. Tetrahedron 41 (1985) 5839
21. Liebeskind L.S., Baysdon S.L., Goedken V., and Chidambaram R. Organometallics 5 (1986) 1086
22. Iyer S., and Liebeskind L.S. J. Am. Chem. Soc. 109 (1987) 2759
23. Huffman M.A., and Liebeskind L.S. J. Am. Chem. Soc. 113 (1991) 2771
24. Kondo T., Taguchi Y., Kaneko Y., Niimi M., and Mitsudo T. Angew. Chem., Int. Ed. 43 (2004) 5369
25. Kondo T., Niimi M., Nomura M., Wada K., and Mitsudo T. Tetrahedron Lett. 48 (2007) 2837
26. For the synthesis of five-membered rings by rhodium-catalyzed [3+2] cycloadditions of cyclopropenones with alkynes, see:. Wender P.A., Paxton T.J., and Williams T.J. J. Am. Chem. Soc. 128 (2006) 14814
27. Murakami M., Itahashi T., and Ito Y. J. Am. Chem. Soc. 124 (2002) 13976
28. Matsuda T., Fujimoto A., Ishibashi M., and Murakami M. Chem. Lett. 33 (2004) 876
29. For the synthesis of eight-membered rings from cyclobutanones, see:. Wender P.A., Correa A.G., Sato Y., and Sun R. J. Am. Chem. Soc. 122 (2000) 7815
30. Tanaka K., and Fu G.C. Org. Lett. 4 (2002) 933
31. Tanaka K., Hagiwara Y., and Noguchi K. Angew. Chem., Int. Ed. 44 (2005) 7260
32. Tanaka K., Hagiwara Y., and Hirano M. Eur. J. Org. Chem. (2006) 3582
33. Hojo D., Noguchi K., Hirano M., and Tanaka K. Angew. Chem., Int. Ed. 47 (2008) 5820
34. Rhodium-catalyzed [4+2] annulations of vinylarylaldehydes with alkenes and alkynes leading to substituted tetralones and 1-naphthols were also reported; see:
35. Tanaka K., Hojo D., Shoji T., Hagiwara Y., and Hirano M. Org. Lett. 9 (2007) 2059
36. For a rhodium-catalyzed homo-[4+2] annulation of vinylbenzaldehyde, see:
37. Kundu K., McCullagh J.V., and Morehead Jr. A.T. J. Am. Chem. Soc. 127 (2005) 16042
38. For reviews, see:
39. Heller B., and Hapke M. Chem. Soc. Rev. 36 (2007) 1085
40. Chopade P.R., and Louie J. Adv. Synth. Catal. 348 (2006) 2307
41. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
42. Varela J.A., and Saà C. Chem. Rev. 103 (2003) 3787
43. Hong P., and Yamazaki H. Synthesis (1977) 50
44. Hong P., and Yamazaki H. Tetrahedron Lett. (1977) 1333
45. Earl R.A., and Vollhardt K.P.C. J. Am. Chem. Soc. 105 (1983) 6991
46. Earl R.A., and Vollhardt K.P.C. J. Org. Chem. 49 (1984) 4786
47. Diversi P., Ingrosso G., Lucherini A., and Malquori S. J. Mol. Catal. 40 (1987) 267
48. Bonaga L.V.R., Zhang H.-C., Gauthier D.A., Reddy I., and Maryanoff B.E. Org. Lett. 5 (2003) 4537
49. Bonaga L.V.R., Zhang H.-C., Moretto A.F., Ye H., Gauthier D.A., Li J., Leo G.C., and Maryanoff B.E. J. Am. Chem. Soc. 127 (2005) 3473
50. Hoberg H., and Oster B.W. Synthesis (1982) 324
51. Hoberg H., and Oster B.W. J. Organomet. Chem. 234 (1982) C35
52. Hoberg H., and Oster B.W. J. Organomet. Chem. 252 (1983) 359
53. Duong H.A., Cross M.J., and Louie J. J. Am. Chem. Soc. 126 (2004) 11438
54. Duong H.A., and Louie J. J. Organomet. Chem. 690 (2005) 5098
55. Duong H.A., and Louie J. Tetrahedron 62 (2006) 7552
56. Yamamoto Y., Takagishi H., and Itoh K. Org. Lett. 3 (2001) 2117
57. Yamamoto Y., Kinpara K., Saigoku T., Takagishi H., Okuda S., Nishiyama H., and Itoh K. J. Am. Chem. Soc. 127 (2005) 605
58. For cationic rhodium(I)/biaryl bisphosphine complex-catalyzed [2+2+2] cycloadditions of alkynes with isocyanates, see:
59. Tanaka K., Wada A., and Noguchi K. Org. Lett. 7 (2005) 4737
60. Tanaka K., Takahashi Y., Suda T., and Hirano M. Synlett (2008) 1724
61. For neutral rhodium(I) complex-catalyzed [2+2+2] cycloadditions of alkynes with isocyanates, see:
62. Flynn S.T., Hasso-Henderson S.E., and Parkins A.W. J. Mol. Catal. 32 (1985) 101
63. Yu R.T., and Rovis T. J. Am. Chem. Soc. 128 (2006) 2782
64. Kondo T., Nomura M., Ura Y., Wada K., and Mitsudo T. Tetrahedron Lett. 47 (2006) 7107
65. Yu R.T., and Rovis T. J. Am. Chem. Soc. 128 (2006) 12370
66. Lee E.E., and Rovis T. Org. Lett. 10 (2008) 1231
67. Yu R.T., Lee E.E., Malik G., and Rovis T. Angew. Chem., Int. Ed. 48 (2009) 2379
68. For examples using stoichiometric transition-metal complexes, see:
69. Takahashi T., Tsai F.-Y., Li Y., Wang H., Kondo Y., Yamanaka M., Nakajima K., and Kotora M. J. Am. Chem. Soc. 124 (2002) 5059
70. Li Y., Matsumura H., Yamanaka M., and Takahashi T. Tetrahedron 60 (2004) 1393
71. Hoberg H., and Burkhart G. Synthesis (1979) 525
72. Young D.D., and Deiters A. Angew. Chem., Int. Ed. 46 (2007) 5187
73. Mukai C., Yoshida T., Sorimachi M., and Odani A. Org. Lett. 8 (2006) 83
74. Saito T., Sugizaki K., Otani T., and Suyama T. Org. Lett. 9 (2007) 1239
75. Aburano D., Yoshida T., Miyakoshi N., and Mukai C. J. Org. Chem. 72 (2007) 6878
76. Yu R.T., and Rovis T. J. Am. Chem. Soc. 130 (2008) 3262
77. Tanaka K., Hagiwara Y., and Noguchi K. Angew. Chem., Int. Ed. 45 (2006) 2734
78. Tanaka K., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 11492
79. Molander G.A., and Retsch W.H. J. Org. Chem. 63 (1998) 5507
80. Eriksson M., Iliefski T., Nilsson M., and Olsson T. J. Org. Chem. 62 (1997) 182