Seasoning materials chemistry by using a well-matured organic concept

Chemistry - A European Journal

Volumn 10, Issue 18, 2004, Pages 4388-4394

  Yokoyama, Yasushi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

Allylic compounds; Allylic strain; Diasteroselectivity; Photochromism

Indexed keywords

MOLECULAR ORIENTATION; ORGANIC COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PHOTOCHROMIC REACTIONS; SYNTHETIC ORGANIC REACTIONS;

PHOTOCHEMICAL REACTIONS;

ALLYL COMPOUND; ETHYLENE DERIVATIVE; NATURAL PRODUCT;

CHEMICAL REACTION; CHEMISTRY; DIASTEREOISOMER; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 4744356691     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400093     Document Type: Review

References (72)

1. a) D. A. Evans, M. M. Morrissey, R. L. Dow, Tetrahedron Lett. 1985, 26, 6005;
2. b) D. A. Evans, M. M. Morrissey, J. Am. Chem. Soc. 1984, 106, 3866;
3. c) J. M. Brown, R. G. Naik, J. Chem. Soc. Chem. Commun. 1982, 348.
4. a) F. Johnson, Chem. Rev. 1968, 68, 375;
5. b) R. W. Hoffmann, Chem. Rev. 1989, 89, 1841.
6. Selected examples of the past one decade concerning the extensively studied allylic 1,3-strain-related stereoselective reactions: epoxidation of olefins: a) R. F. W. Jackson, S. P. Standen, W. Clegg, A. McCamley, J. Chem. Soc. Perkin Trans. 1 1995, 141;
7. b) D. Poisson, G. Cure, G. Solladie, G. Hanquet, Tetrahedron Lett. 2001, 42, 3745;
8. c) W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Moeller, D. Sloboda-Rozner, R. Zhang, J. Org. Chem. 2003, 68, 1721;
9. ene reaction: d) W. Adam, B. Nestler, A. Pastor, T. Wirth, Tetrahedron Lett. 1998, 39, 2625;
10. e) W. Adam, N. Bottke, O. Krebs, I. Lykakis, M. Orfanopoulos, M. Stratakis, J. Am. Chem. Soc. 2002, 124, 14403;
11. electrophilic/nucleophilic alkylation: f) Y. G. Lee, K. Ishimaru, H. Iwasaki, K. Ohkata, K. Akiba, J. Org. Chem. 1991, 56, 2058;
12. g) L. E. Burgess, A. I. Meyers, J. Am. Chem. Soc. 1991, 113, 9858;
13. h) S. Yoshida, T. Yamanaka, T. Miyake, Y. Moritani, H. Ohmizu, T. Iwasaki, Tetrahedron 1997, 53, 9585;
14. i) M. Fernandez-Zertuche, R. Robledo-Perez, M. E. Meza-Avina, M. Ordonez-Palacios, Tetrahedron Lett. 2002, 43, 3777;
15. hydride reduction/protonation: j) Y. Moritani, C. Fukushima, T. Miyagishima, H. Ohmizu, T. Iwasaki, Bull. Chem. Soc. Jpn. 1996, 69, 2281;
16. photochemical [2+2] oxetane/dioxetane formation: k) T. Bach, K. Joedicke, K. Kather, R. Froehlich, J. Am. Chem. Soc. 1997, 119, 2437;
17. l) W. Adam, C. R. Saha-Moeller, S. B. Schambony, J. Am. Chem. Soc. 1999, 121, 1834;
18. m) W. Adam, K. Peters, E. M. Peters, V. R. Stegmann, J. Am. Chem. Soc. 2000, 122, 2958;
19. Diels-Alder reaction: n) W. Adam, J. Glaeser, K. Peters, M. Prein, J. Am. Chem. Soc. 1995, 117, 9190;
20. o) G. T. Crisp, M. G. Gebauer, J. Org. Chem. 1996, 61, 8425;
21. p) C. Aneres, J. P. Duque-Soladana, R. Pedrosa, J. Org. Chem. 1999, 64, 4273;
22. q) W. V. Murray, S. Sun, I. J. Turchi, F. K. Brown, A. D. Gauthier, J. Org. Chem. 1999, 64, 5930;
23. dihydroxylation of olefins: r) P. M. Koskinen, M. P. Ari, Tetrahedron Lett. 1997, 38, 3103;
24. 1,3-dipolar cycloadditions: s) M. Ihara, M. Takahashi, K. Fukumoto, T. Kametani, J. Chem. Soc. Perkin Trans. 1 1989, 2215;
25. t) M. ihara, Y. Tanaka, N. Takahashi, Y. Tokunaga, K. Fukumoto, J. Chem. Soc. Perkin Trans. 1 1997, 3043;
26. radical cyclization: u) A. M. Gomez, L. J. Cristobal, B. Fraser-Reid, J. Org. Chem. 1995, 60, 3859;
27. theoretical studies: v) L. F. Tietze, G. Schulz, Liebigs Ann. 1996, 1575;
28. w) J. Haller, T. Strassner, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 8031;
29. x) M. Cui, W. Adam, J. H. Shen, X. M. Luo, X. J. Tan, K. X. Chen, R. Y. Ji, H. L. Jiang, J. Org. Chem. 2002, 67, 1427.
30. a) A. B. Smith, III, Y. Yokoyama, D. M. Huryn, N. K. Dunlap, Tetrahedron Lett. 1987, 28, 3659.
31. b) A. B. Smith, III, Y. Yokoyama, N. K. Dunlap, A. Hadener, C. Tamm, Tetrahedron Lett. 1987, 28, 3663.
32. a) W. C. Still, K. P. Darst, J. Am. Chem. Soc. 1980, 102, 7387;
33. b) W. C. Still, K. R. Shaw, Tetrahedron Lett. 1981, 22, 3725.
34. D. J. Morgans, Jr., Tetrahedron Lett. 1981, 22, 3721.
35. A. Pelter, K. Smith, M. G. Hutchings, K. Rowe, J. Chem. Soc. Perkin Trans. 1 1975, 129.
36. a) Y. Yokoyama, H. Kawashima, H. Masaki, Chem. Lett. 1989, 453;
37. b) Y. Yokoyama, H. Kawashima, M. Kohno, Y. Ogawa, S. Uchida, Tetrahedron Lett. 1991, 32, 1479;
38. c) Y. Yokoyama, Y. Terada, H. Kawashima, Bull. Chem. Soc. Jpn. 1991, 64, 2563.
39. Y. Yokoyama, K. Tsuchikura, Tetrahedron Lett. 1992, 33, 2823.
40. Y. Yokoyama, Chem. Rev. 2000, 100, 1717.
41. Photochromism: Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam (The Netherlands) 1990.
42. M. Irie, Chem. Rev. 2000, 100, 1685.
43. a) S. M. Shrestha, H. Nagashima, Y. Yokoyama, Y. Yokoyama, Bull. Chem. Soc. Jpn. 2003, 76, 363;
44. b) A. Peters, C. Vitols, R. McDonald, N. R. Branda, Org. Chem. 2003, 5, 1183.
45. a) Y. Yokoyama, T. Goto, T. Inoue, M. Yokoyama, Y. Kurita, Chem. Lett. 1988, 1049;
46. b) Y. Yokoyama, T. Inoue, M. Yokoyama, T. Goto, T. Iwai, N. Kera, I. Hitomi, Y. Kurita, Bull. Chem. Soc. Jpn. 1994, 67, 3297;
47. c) J. Kiji, T. Okano, H. Kitamura, Y. Yokoyama, S. Kubota, Y. Kurita, Bull. Chem. Soc. Jpn. 1995, 68, 616;
48. d) Y. Yokoyama, T. Iwai, N. Kera, I. Hitomi, Y. Kurita, Chem. Lett. 1990, 263;
49. e) S. Uchida, S. Yamada, Y. Yokoyama, Y. Kurita, Bull. Chem. Soc. Jpn. 1995, 68, 1677.
50. a) Y. Yokoyama, T. Tanaka, T. Yamane, Y. Kurita, Chem. Lett. 1991, 1125;
51. b) Y. Yokoyama, T. Sagisaka, Y. Mizuno, Y. Yokoyama, Chem. Lett. 1996, 587;
52. c) F. Matsui, H. Taniguchi, Y. Yokoyama, K. Sugiyama, Y. Kurita, Chem. Lett. 1994, 1869.
53. Y. Yokoyama, T. Yamane, Y. Kurita, J. Chem. Soc. Chem. Commun. 1991, 1722.
54. Y. Yokoyama, T. Iwai, Y. Yokoyama, Y. Kurita, Chem. Lett. 1994, 225.
55. Y. Yokoyama, Y. Shimizu, S. Uchida, Y. Yokoyama, J. Chem. Soc. Chem. Commun. 1995, 785.
56. Y. Yokoyama, S. Uchida, Y. Yokoyama, Y. Sugawara, Y. Kurita, J. Am. Chem. Soc. 1996, 118, 3100.
57. Y. Yokoyama, H. Shiraishi, Y. Tani, Y. Yokoyama, Y. Yamaguchi, J. Am. Chem. Soc. 2003, 125, 7194.
58. a) T. Yamaguchi, K. Uchida, M. Irie, J. Am. Chem. Soc. 1997, 119, 6066;
59. b) T. Kodani, K. Matsuda, T. Yamada, S. Kobatake, M. Irie, J. Am. Chem. Soc. 2000, 122, 9631;
60. c) K. Matsuda, S. Yamamoto, M. Irie, Chem. Lett. 2001, 7291; E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. 2001, 113, 1802; Angew. Chem. Int. Ed. 2001, 40, 1752.
61. c) K. Matsuda, S. Yamamoto, M. Irie, Chem. Lett. 2001, 7291; E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. 2001, 113, 1802; Angew. Chem. Int. Ed. 2001, 40, 1752.
62. c) K. Matsuda, S. Yamamoto, M. Irie, Chem. Lett. 2001, 7291; E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. 2001, 113, 1802; Angew. Chem. Int. Ed. 2001, 40, 1752.
63. a) E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551;
64. b) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092; Angew. Chem. Int. Ed. 1998, 37, 1986.
65. b) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092; Angew. Chem. Int. Ed. 1998, 37, 1986.
66. M. Kose, M. Shinoura, Y. Yokoyama, Y. Yokoyama, to be published.
67. Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim (Germany), 2001.
68. a) Y. Yokoyama, T. Sagisaka, Chem. Lett. 1997, 687;
69. b) T. Sagisaka, Y. Yokoyama, Bull. Chem. Soc. Jpn. 2000, 73, 191.
70. a) M. Saito, Y. Yokoyama, Y. Yokoyama, Chem. Lett. 2003, 32, 806;
71. b) M. Saito, K. Musha, T. Ikejima, S. Ozawa, Y. Yokoyama, Y. Yokoyama, Kobunshi Ronbunshu 2003, 60, 581;
72. c) M. Saito, K. Musha, Y. Yokoyama, Y. Yokoyama, Bull. Chem. Soc. Jpn. 2003, 76, 2423.