Catalytic asymmetric carbon-carbon bond forming reactions using chiral silver complexes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 63, Issue 9, 2005, Pages 888-898

  Yanagisawa, Akira ^a   Yamamoto, Hisashi ^b  

^a CHIBA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Aldol reaction; Allylation; Allylsilane; Allyltin; Asymmetric reaction; BINAP; Chiral silver complex; Nitroso aldol reaction; Silyl enolate; Tin enolate

Indexed keywords

CARBON INORGANIC COMPOUNDS; CATALYSIS; CATALYSTS; CHEMICAL BONDS; NITROGEN COMPOUNDS; SILVER COMPOUNDS;

CARBONYL COMPOUNDS; ENANTIOSELECTIVE ALLYLATION;

ALCOHOLS;

EID: 28044445450     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.63.888     Document Type: Article

References (86)

1. (a) "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 1999, Vols I-IIII;
2. (b) "Lewis Acids in Organic Synthesis" ed. by H. Yamamoto, Wiley-VCH, Weinheim, 2000, Vols 1 and 2;
3. "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 2004, Supplements 1 and 2
4. A. Yanagisawa, M. Morodome, H. Nakashima, H. Yamamoto, Synlett, 1997, 1309
5. (a) D. R. Rae, "Encyclopedia of Reagents for Organic Synthesis" ed. by L. A. Paquette, John Wiley & Sons, Chichester, 1995, Vol. 6, p 4461;
6. (b) J. C. Lanter, "Encyclopedia of Reagents for Organic Synthesis" ed. by L. A. Paquette, John Wiley & Sons, Chichester, 1995, Vol. 6, p 4469;
7. (c) L.-G. Wistrand, "Encyclopedia of Reagents for Organic Synthesis" ed. by L. A. Paquette, John Wiley & Sons, Chichester, 1995, Vol. 6, p 4472;
8. (d) T. H. Black, "Encyclopedia of Reagents for Organic Synthesis" ed. by L. A. Paquette, John Wiley & Sons, Chichester, 1995, Vol. 6, p 4476
9. (a) T. Hayashi, Y. Uozumi, A. Yamazaki, M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron Lett., 32, 2799 (1991);
10. (b) M. Sawamura, H. Hamashima, Y. Ito, J. Org. Chem., 55, 5935 (1990)
11. R. Grigg, Tetrahedron: Asymmetry, 6, 2475 (1995)
12. (a) W. R. Roush, "Comprehensive Organic Synthesis" eds. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, Oxford, 1991, Vol. 2, p 1;
13. (b) Y. Yamamoto, N. Asao, Chem. Rev., 93, 2207 (1993);
14. (c) T. Bach, Angew. Chem., Int. Ed. Engl., 33, 417 (1994);
15. (d) D. Hoppe, "Houben-Weyl: Methods of Organic Chemistry" eds. by G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, Vol. E 21, p 1357;
16. (e) A. H. Hoveyda, J. P. Morken, Angew. Chem., Int. Ed. Engl., 35, 1262 (1996);
17. (f) P. G. Cozzi, E. Tagliavini, A. Umani-Ronchi, Gazz. Chim. Ital., 127, 247 (1997);
18. (g) A. Yanagisawa, "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 1999, Vol. 2, p 965;
19. (h) S. E. Denmark, N. G. Almstead, "Modern Carbonyl Chemistry" ed. by J. Otera, Wiley-VCH, Weinheim, 2000, Chapter 10, p 299;
20. (i) S. R. Chemler, W. R. Roush, "Modern Carbonyl Chemistry" ed. by J. Otera, Wiley-VCH, Weinheim, 2000, Chapter 11, p 403;
21. (j) S. E. Denmark, J. Fu, Chem. Rev., 103, 2763 (2003);
22. (k) A. Yanagisawa, "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 2004, Supplement 2, p 97
23. A. Yanagisawa, H. Inoue, M. Morodome, H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993)
24. (a) A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc., 118, 4723 (1996);
25. (b) A. Yanagisawa, H. Nakashima, Y. Nakatsuka, A. Ishiba, H. Yamamoto, Bull. Chem. Soc. Jpn., 74, 1129 (2001)
26. A. Yanagisawa, A. Ishiba, H. Nakashima, H. Yamamoto, Synlett, 1997, 88
27. (a) Y. Yamamoto, H. Yatagai, Y. Naruta, K. Maruyama, J. Am. Chem. Soc., 102, 7107 (1980);
28. (b) Y. Yamamoto, H. Yatagai, Y. Ishihara, N. Maeda, K. Maruyama, Tetrahedron, 40, 2239 (1984)
29. (a) G. Courtois, L. Miginiac, J. Organomet. Chem., 69, 1 (1974);
30. (b) H. Yasuda, A. Nakamura, J. Organomet. Chem., ibid., 285, 15 (1985)
31. A. Yanagisawa, Y. Nakatsuka, H. Nakashima, H. Yamamoto, Synlett, 1997, 933
32. T.-P. Loh, J.-R. Zhou, Tetrahedron Lett., 41, 5261 (2000)
33. M. Shi, W.-S. Sui, Tetrahedron: Asymmetry, 11, 773 (2000)
34. (a) K. Furuta, M. Mouri, H. Yamamoto, Synlett, 1991, 561;
35. (b) K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc., 115, 11490 (1993)
36. (a) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron, 49, 1783 (1993);
37. (b) D. R. Gauthier, Jr., E. M. Carreira, Angew. Chem., Int. Ed. Engl., 35, 2363 (1996)
38. (a) A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, H. Yamamoto, Angew. Chem. Int. Ed., 38, 3701 (1999).
39. (b) K. Fujii, K. Maki, M. Kanai, M. Shibasaki, Org. Lett., 5, 733 (2003)
40. (a) A. Yanagisawa, Y. Nakatsuka, K. Asakawa, H. Kageyama, H. Yamamoto, Synlett, 2001, 69;
41. (b) A. Yanagisawa, Y. Nakatsuka, K. Asakawa, M. Wadamoto, H. Kageyama, H. Yamamoto, Bull. Chem. Soc. Jpn., 74, 1477 (2001)
42. M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem., 68, 5593 (2003)
43. Y. Nishigaichi, A. Takuwa, Chem. Lett., 1994, 1429
44. G. E. Keck, K. A. Savin, E. N. K. Cressman, D. E. Abbott, J. Org. Chem., 59, 7889 (1994)
45. "Modern Aldol Reactions" ed. by R. Mahrwald, Wiley-VCH, Weinheim, 2004, Vols 1 and 2
46. (a) C. Gennari, "Comprehensive Organic Synthesis", eds. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, Oxford, 1991, Vol. 2, p 629;
47. (b) T. K. Hollis, B. Bosnien, J. Am. Chem. Soc., 117, 4570 (1995);
48. (c) M. Braun, "Houben-Weyl: Methods of Organic Chemistry", eds. by G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, Vol. E 21, p 1730;
49. (d) S. G. Nelson, Tetrahedron: Asymmetry, 9, 357 (1998);
50. (e) H. Gröger, E. M. Vogl, M. Shibasaki, Chem. Eur. J., 4, 1137 (1998);
51. (f) R. Mahrwald, Chem. Rev., 99, 1095 (1999);
52. (g) E. M. Carreira, "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 1999, Vol. 3, p 997;
53. (h) P. Arya, H. Qin, Tetrahedron, 56, 917 (2000);
54. (i) T. D. Machajewski, C.-H. Wong, Angew. Chem. Int. Ed., 39, 1353 (2000);
55. (j) E. M. Carreira, "Modern Carbonyl Chemistry" ed. by J. Otera, Wiley-VCH, Weinheim, 2000, chapter 8, p 227
56. (a) S. E. Denmark, R. A. Stavenger, X. Su, K.-T. Wong, Y. Nishigaichi, Pure Appl. Chem. 70, 1469 (1998);
57. (b) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 33, 432 (2000)
58. (a) H. Gröger, J. Wilken, Angew. Chem. Int. Ed., 40, 529 (2001);
59. (b) B. List, Synlett, 2001, 1675
60. A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc., 119, 9319 (1997)
61. (a) M. Pereyre, B. Bellegarde, J. Mendelsohn, J. Valade, J. Organomet. Chem., 11, 97 (1968);
62. (b) I. F. Lutsenko, Y. I. Baukov, I. Y. Belavin, J. Organomet. Chem., ibid., 24, 359 (1970);
63. (c) S. S. Labadie, J. K. Stille, Tetrahedron, 40, 2329 (1984);
64. (d) K. Kobayashi, M. Kawanisi, T. Hitomi, S. Kozima, Chem. Lett., 1984, 497
65. A. Yanagisawa, Y. Matsumoto, K. Asakawa, H. Yamamoto, Tetrahedron, 58, 8331 (2002)
66. A. Yanagisawa, Y. Matsumoto, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc., 121, 892 (1999)
67. (a) M. Ohkouchi, M. Yamaguchi, T. Yamagishi, Enantiomer, 5, 71 (2000);
68. (b) M. Ohkouchi, D. Masui, M. Yamaguchi, T. Yamagishi, J. Mol. Catal. A: Chem., 170, l (2001);
69. (c) M. Ohkouchi, D. Masui, M. Yamaguchi, T. Yamagishi, J. Mol. Catal. A: Chem., 2002, No. 2, 223
70. N. Ozasa, M. Wadamoto, K. Ishihara, H. Yamamoto, Synlett, 2003, 2219
71. (a) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc., 120, 4548 (1998);
72. (b) D. Ferraris, B. Young, C. Cox, T. Dudding, W. J. Drury, III, L. Ryzhkov, A. E. Taggi, T. Lectka, J. Am. Chem. Soc., ibid., 124, 67 (2002)
73. N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 126, 3734 (2004)
74. (a) W. J. Drury, III, D. Ferraris, C. Cox, B. Young, T. Lectka, J. Am. Chem. Soc., 120, 11006 (1998);
75. (b) S. Yao, X. Fang, K. A. Jøergensen, Chem. Commun., 1998, 2547
76. S. Yao, M. Johannsen, R. G. Hazell, K. A. Jørgensen, Angew. Chem. Int. Ed., 37, 3121 (1998)
77. J. M. Longmire, B. Wang, X. Zhang, J. Am. Chem. Soc., 124, 13400 (2002)
78. N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 125, 4018 (2003)
79. Y. Yamashita, H. Ishitani, S. Kobayashi, Can. J. Chem., 78, 666 (2000)
80. (a) N. Momiyama, H. Yamamoto, Angew. Chem. Int. Ed., 41, 2986 (2002);
81. (b) N. Momiyama, H. Yamamoto, idem, Org. Lett., 4, 3579 (2002)
82. (a) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc., 125, 6038 (2003);
83. (b) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc., ibid., 126, 5962 (2004)
84. (a) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl. Acad. Sci. U.S.A., 101, 5374 (2004);
85. (b) P. Merino, T. Tejero, Angew. Chem. Int. Ed., 43, 2995 (2004)
86. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc., 126, 5360 (2004)