Recent advances in asymmetric nitroso Diels-Alder reactions

European Journal of Organic Chemistry

Volumn , Issue 9, 2006, Pages 2031-2043

  Yamamoto, Yuhei ^a   Yamamoto, Hisashi ^b,c  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

^c International Advisory Board of European Journal of Organic Chemistry   (United States)

Author keywords

Amino alcohols; Asymmetric catalysis; Diels Alder reactions; Natural product synthesis; Nitroso compounds

Indexed keywords

EID: 33646419797     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500847     Document Type: Short Survey

References (88)

1. For a recent review on nitroso chemistry see: a) H. Yamamoto, N. Momiyama, Chem. Commun. 2005, 3514-3525.
2. For reviews on nitroso Diels-Alder reaction see: a) H. Waldmann, Synthesis 1994, 535-551;
3. b) J. Streith, A. Defoin, Synthesis 1994, 1107-1117;
4. c) J. Streith, A. Defoin, Synlett 1996, 189-200;
5. d) P. F. Vogt, M. J. Miller, Tetrahedron 1998, 54, 1317-1348.
6. a) W. Oppolzer, O. Tamura, Tetrahedron Lett. 1990, 31, 991-994;
7. b) W. Oppolzer, O. Tamura, G. Sundarababu, M. Signer, J. Am. Chem. Soc. 1992, 114, 5900-5902.
8. For a review on nitroso ene reaction see: W. Adam, O. Krebs, Chem. Rev. 2003, 103, 4131-4146.
9. a) N. Momiyama, H. Yamamoto, Angew. Chem. Int. Ed. 2002, 41, 2986-2988;
10. N. Momiyama, H. Yamamoto, Angew. Chem. Int. Ed. 2002, 41, 3313;
11. b) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6038-6039;
12. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 6498.
13. For reviews on approaches to this class of compounds see: a) P. G. Tsoungas, Heterocycles 2002, 57, 915-953;
14. b) P. G. Tsoungas, Heterocycles 2002, 57, 1149-1178.
15. Recent advances on approaches to this class of compounds: c) R. Pulz, S. Cicchi, A. Brandi, H.-U. Reissig, Eur. J. Org. Chem. 2003, 1153-1156;
16. d) M. D. Ganton, M. A. Kerr, J. Org. Chem. 2004, 69, 8554-8557;
17. e) M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc. 2005, 127, 5764-5765;
18. f) S. Kumarn, D. M. Shaw, D. A. Longbottom, S. V. Ley, Org. Lett. 2005, 7, 4189-4191.
19. a) O. Wichterle, Collect. Czech. Chem. Commun. 1947, 12, 292-304;
20. b) Y. A. Arbuzov, Dokl. Akad. Nauk SSSR 1948, 60, 993-996.
21. a) H. Nitsch, G. Kresze, Angew. Chem. 1976, 88, 801;
22. Angew. Chem. Int. Ed. Engl. 1976, 15, 760;
23. b) H. Felber, G. Kresze, R. Prewo, A. Vasella, Helv. Chim. Acta 1986, 69, 1137-1146.
24. G. W. Kirby, M. Nazeer, Tetrahedron Lett. 1988, 29, 6173-6174.
25. S. B. King, B. Ganem, J. Am. Chem. Soc. 1991, 113, 5089-5090.
26. T. Hudlicky, H. F. Olivio, J. Am. Chem. Soc. 1992, 114, 9694-9696.
27. J. Li, F. Lang, B. Ganem, J. Org. Chem. 1998, 63, 3403-3410.
28. A. Miller, T. McC. Peterson, G. Procter, Synlett 1989, 32-34.
29. T. Fatig, J. Soulié, J.-Y. Lallemand, L. Ricard, Tetrahedron: Asymmetry 1999, 10, 2165-2174.
30. A. J. Pearson, K. Srinivasan, J. Org. Chem. 1992, 57, 3965-3973.
31. S. Aoyagi, R. Tanaka, M. Naruse, C. Kibayashi, J. Org. Chem. 1998, 63, 8397-8406.
32. For discussions on regioselectivity in NDA reaction, see: a) D. L. Boger, M. Patel, F. Takusagawa, J. Org. Chem. 1985, 50, 1911-1916;
33. [2c].
34. a) M. J. Mulvihill, J. L. Gage, M. J. Miller, J. Org. Chem. 1998, 63, 3357-3363;
35. b) F. Li, J. B. Brogan, J. L. Gage, D. Zhang, M. J. Miller, J. Org. Chem. 2004, 69, 4538-4540;
36. c) F. Li, N. C. Warshakoon, M. J. Miller, J. Org. Chem. 2004, 69, 8836-8841.
37. G. E. Keck, Tetrahedron Lett. 1978, 19, 4767-4770.
38. a) T. P. Burkholder, P. L. Fuchs, J. Am. Chem. Soc. 1990, 112, 9601-9613;
39. b) G. E. Keck, D. R. Romer, J. Org. Chem. 1993, 58, 6083-6089;
40. c) C. Kibayashi, S. Aoyagi, Synlett 1995, 873-879;
41. d) T. Ozawa, S. Aoyagi, C. Kibayashi, J. Org. Chem. 2001, 66, 3338-3347;
42. e) T. Sato, S. Aoyagi, C. Kibayashi, Org. Lett. 2003, 5, 3839-3842.
43. P. R. Blakemore, S.-K. Kim, V. K. Schulze, J. D. White, A. F. T. Yokochi, J. Chem. Soc., Perkin Trans. 1 2001, 1831-1845.
44. For a review see: B. R. Bear, S. M. Sparks, K. J. Shea, Angew. Chem. Int. Ed. 2001, 40, 820-849; and references cited therein.
45. a) S. M. Sparks, J. D. Vargas, K. J. Shea, Org. Lett. 2000, 2, 1473-1475;
46. b) C. P. Chow, K. J. Shea, S. M. Sparks, Org. Lett. 2002, 4, 2637-2640;
47. c) S. M. Sparks, C. P. Chow, L. Zhu, K. J. Shea, J. Org. Chem. 2004, 69, 3025-3035.
48. For direct observation of an acyl nitroso species see: A. D. Cohen, Bu.-B. Zeng, S. B. King, J. P. Toscano, J. Am. Chem. Soc. 2003, 125, 1444-1445. and references cited therein.
49. G. W. Kirby, J. G. Sweeny, J. Chem. Soc., Chem. Commun. 1962, 704-711.
50. a) K. R. Flower, A. P. Lightfoot, H. Wan, A. Whiting, Chem. Commun. 2001, 1812-1813.
51. also see: b) S. Iwasa, K. Tajima, S. Tsushima, H. Nishiyama, Tetrahedron Lett. 2001, 42, 5897-5899.
52. K. R. Flower, A. P. Lightfoot, H. Wan, A. Whiting, J. Chem. Soc., Perkin Trans. 1 2002, 2058-2064.
53. X. Yao, M. Qui, W. Lü, H. Chen, Z. Zheng, Tetrahedron: Asymmetry 2001, 12, 197-204.
54. C. P. Chow, K. J. Shea, J. Am. Chem. Soc. 2005, 127, 3678-3679.
55. a) J. Chang, M. D. Seider, R. G. Bergman, J. Am. Chem. Soc. 1989, 111, 3258-3271;
56. b) J.-L. Liang, J.-S. Huang, Z.-Y. Zhou, K.-K. Cheung, C.-M. Che, Chem. Eur. J. 2001, 7, 2306-2317;
57. c) J. Lee, B. Twamley, G. B. Richter-Addo, Dalton Trans. 2004, 189-196.
58. A. P. Lightfoot, R. G. Pritchard, H. Wan, J. E. Warren, A. Whiting, Chem. Commun 2002, 2072-2073.
59. For reviews on dinitroso and polynitroso compounds, see: B. G. Gowenlock, G. B. Richter-Addo, Chem. Soc. Rev. 2005, 34, 797-809, and references cited therein.
60. R. S. Srivastava, K. M. Nicholas, J. Am. Chem. Soc. 1997, 119, 3302-3310.
61. X. Ding, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 2003, 32, 582-583.
62. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5360-5361.
63. For reviews on coordination of C-nitroso compounds with metals, see: a) M. Cameron, B. G. Gowenlock, Chem. Soc. Rev. 1990, 19, 355-379;
64. b) J. Lee, L. Chen, A. H. West, G. B. Richter-Addo, Chem. Rev. 2002, 102, 1019-1065.
65. Recent reports in this area: c) J. M. O'Connor, K. D. Bunker, Organometallics 2003, 22, 5268-5273;
66. d) X. Li, C. D. Incarvito, T. Vogel, R. H. Crabtree, Organometallics 2005, 24, 3066-3073;
67. e) R. S. Srivastava, M. A. Khan, K. M. Nicholas, J. Am. Chem. Soc. 2005, 127, 7278-7279.
68. For O-binding see: a) G.-E. Matsubayashi, K. Nakatsu, Inorg. Chim. Acta 1982, 64, L163;
69. b) S. Hu, D. M. Thompson, P. O. Ikekwere, R. J. Barton, K. E. Johnson, B. E. Robertson, Inorg. Chem. 1989, 28, 4552-4554;
70. c) L.-S. Wang, L. Chen, M. A. Khan, G. B. Richter-Addo, Chem. Commun. 1996, 323-324;
71. d) S. J. Fox, L. Chen, M. A. Kahn, G. B. Richter-Addo, Inorg. Chem. 1997, 36, 6465-6467.
72. Recently, interesting methods for activation of α-acetoxynitroso compounds were reported. see: a) G. Calvet, M. Dussaussois, N. Blanchard, C. Kouklovsky, Org. Lett. 2004, 6, 2449-2451;
73. b) G. Calvet, R. Guillot, N. Blanchard, C. Kouklovsky, Org. Biomol. Chem. 2005, 3, 4395-4401.
74. Y. Yamamoto, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 4128-4129.
75. For a review on biaryl-type bisphosphane ligands see: H. Shimizu, I. Nagasaki, T. Saito, Tetrahedron 2005, 61, 5405-5432.
76. Y. Yamamoto, H. Yamamoto, Angew. Chem. 2005, 117, 7244-7247;
77. Angew. Chem. Int. Ed. 2005, 44, 7082-7085.
78. For reviews see: a) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058;
79. Angew. Chem. Int. Ed. 2004, 43, 2995-2997;
80. b) J. M. Jahey, Angew. Chem. 2005, 117, 4364-4372;
81. Angew. Chem. Int. Ed. 2005, 44, 4292-4300;
82. Recent advances in this area: c) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 1080-1081;
83. d) H.-M. Guo, L. Cheng, L.-F. Cun, L.-Z, Gong, A.-Q. Mi, Y.-Z. Jiang, Chem. Commun, 2006, advanced article.
84. a) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963;
85. also see: b) Y. Hayashi, J. Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, S. Mitsuru, D. Hashizume, H. Koshino, Adv. Synth. Catal. 2004, 346, 1435-1439;
86. c) H. Sundén, N. Dahlin, I. Ibrahem, H. Adolfsson, A. Córdova, Tetrahedron Lett. 2005, 46, 3385-3389.
87. a) J. S. Baum, H. G. Viehe, J. Org. Chem. 1976, 41, 183-187;
88. b) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.