"Designer acids": Combined acid catalysis for asymmetric synthesis

Angewandte Chemie - International Edition

Volumn 44, Issue 13, 2005, Pages 1924-1942

  Yamamoto, Hisashi ^a   Futatsugi, Kentaro ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Asymmetric catalysis; Br nsted acids; Catalysis design; Cooperative effects; Lewis acids

Indexed keywords

ACIDS; CHEMICAL ANALYSIS; SYNTHESIS (CHEMICAL);

BRONSTED ACID ASSISTED BRONSTED ACID (BBA); BRONSTED ACID ASSISTED LEWIS ACID (BLA); LEWIS ACID ASSISTED BRONSTED ACID (LBA); LEWIS ACID ASSISTED LEWIS ACID (LLA);

CATALYSIS;

EID: 16844374787     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460394     Document Type: Review

References (103)

1. a) Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000;
2. b) Lewis Acid Reagents: A Practical Approach (Ed.: H. Yamamoto), Oxford University Press, Oxford, 1999.
3. J. Ren, C. J. Cramer, R. R. Squires, J. Am. Chem. Soc. 1999, 121, 2633-2634.
4. J. H. Clark, Acc. Chem. Res. 2002, 35, 791-797.
5. E. Negishi, Chem. Eur. J. 1999, 5, 411-420.
6. Y. Pocker, K. D. Stevens, J. J. Champoux, J. Am. Chem. Soc. 1969, 91, 4199-4205; Y. Pocker, K. D. Stevens, J. Am. Chem. Soc. 1969, 91, 4205-4210.
7. Y. Pocker, K. D. Stevens, J. J. Champoux, J. Am. Chem. Soc. 1969, 91, 4199-4205; Y. Pocker, K. D. Stevens, J. Am. Chem. Soc. 1969, 91, 4205-4210.
8. G. A. Olah, G. K. S. Prakash, J. Sommer, Science 1979, 206, 13-20.
9. K. Maruoka, M. Sakurai, J. Fujiwara, H. Yamamoto, Tetrahedron Lett. 1986, 27, 4895-4898.
10. a) K. Furuta, Y. Miwa, K. Iwanaga, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 6254-6255;
11. b) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483;
12. c) K. Furuta, A. Kanematsu, H. Yamamoto, S. Takaoka, Tetrahedron Lett. 1989, 30, 7231-7232;
13. d) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042;
14. e) K. Furuta, T. Maruyama, H. Yamamoto, Synlett 1991, 439-440;
15. f) K. Furuta, M. Mouri, H. Yamamoto, Synlett 1991, 561-562;
16. g) K. Ishihara, Q. Gao, H. Yammamoto, J. Org. Chem. 1993, 58, 6917-6919;
17. h) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951-1952;
18. i) K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 11 490-11 495;
19. j) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413.
20. a) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562;
21. b) K. Ishihara, H. Kurihara, M. Matsumoto, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 6920-6930.
22. K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050.
23. K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10 520-10 524.
24. Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507.
25. a) S. Kobayashi, M. Murakami, T. Harada, T. Mukaiyama, Chem. Lett. 1991, 1341-1344;
26. b) V. K. Aggarwal, E. Anderson, R. Giles, A. Zaparucha, Tetrahedron: Asymmetry 1995, 6, 1301-1306.
27. a) E. J. Corey, T. Shibata, T. W. Lee, J. Am. Chem. Soc. 2002, 124, 3808-3809;
28. b) D. H. Ryu, T. W. Lee, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 9992-9993.
29. a) D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 6388-6390;
30. b) G. Zhou, Q-Y. Hu, E. J. Corey, Org. Lett. 2003, 5, 3979-3982.
31. a) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084;
32. b) S. Kobayashi, H. Ishitani, I. Hachiya, M. Araki, Tetrahedron 1994, 50, 11 623-11 636.
33. a) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084;
34. b) S. Kobayashi, H. Ishitani, I. Hachiya, M. Araki, Tetrahedron 1994, 50, 11 623-11 636.
35. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357-7360.
36. S. Kobayashi, M. Kawamura, J. Am. Chem. Soc. 1998, 120, 5840-5841.
37. M. Oishi, S. Aratake, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 8271-8272.
38. K. Ishihara, J. Kobayashi, K. Inanaga, H. Yamamoto, Synlett 2001, 3, 394-396.
39. H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. 1998, 110, 3369-3372; Angew. Chem. Int. Ed. 1998, 37, 3186-3188.
40. H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. 1998, 110, 3369-3372; Angew. Chem. Int. Ed. 1998, 37, 3186-3188.
41. a) S. Kobayashi, H. Ishitani, Chiralily 2000, 12, 540-543;
42. b) H. Ishitani, S. Komiyama, Y. Hasegawa, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 762-766.
43. H. Hanawa, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 1708-1709.
44. a) R. Mahrwald, Org. Lett. 2000, 2, 4011-4012;
45. b) R. Mahrwald, B. Ziemer, Tetrahedron Lett. 2003, 44, 4459-4461.
46. a) M. Reilly, T. Oh, Tetrahedron Lett. 1994, 35, 7209-7212;
47. b) M. Reilly, T. Oh, Tetrahedron Lett. 1995, 36, 217-220;
48. c) M. Reilly, T. Oh, Tetrahedron Lett. 1995, 36, 221-224.
49. a) For a review, see: M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2209;
50. 3tris(binaphtoxide)] (YLB) was reported as an effective catalyst for the asymmetric 1,4-addition of o-alkyl hydroxylamine to enones: N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 16178-16179.
51. N. Yoshikawa, Y. M. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168-4178.
52. N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466-2467.
53. a) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105; Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
54. a) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105; Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
55. b) S. Shimizu, K. Ohori, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 7547-7551.
56. Y. Xu, K. Ohori, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 55, 2585-2588.
57. S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 8857-8867.
58. S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
59. N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169-2178.
60. K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5647-5650; Angew. Chem. Int. Ed. 2003, 42, 5489-5492.
61. K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5647-5650; Angew. Chem. Int. Ed. 2003, 42, 5489-5492.
62. a) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12 003-12 004;
63. b) B. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367-3368;
64. c) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497-2500;
65. d) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339;
66. e) B. M. Trost, T. Mino, J. Am. Chem. Soc. 2003, 125, 2410-2411.
67. For the application of MAO as a Lewis acidic reagent in organic synthesis, see: M. Akakura, H. Yamamoto, Synlett 1997, 277-278, and references therein.
68. a) P. Pino, M. Galimberti, P. Prada, G. Consiglio, Macromol. Chem. 1990, 191, 1677-1688;
69. b) P. Pino, P. Cioni, J. Wei, J. Am. Chem. Soc. 1987, 109, 6189-6191;
70. c) for other examples of the use of enantiomerically pure metallocene/MAO catalysts, see: G. W. Coates in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 1329-1349, and references therein.
71. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1996, 118, 1577-1578; E. Negishi, Chem. Eur. J. 1999, 5, 411-420.
72. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1996, 118, 1577-1578; E. Negishi, Chem. Eur. J. 1999, 5, 411-420.
73. T. Ishiyama, T. Ahiko, N. Miyaura, J. Am. Chem. Soc. 2002, 124, 12 414-12 415.
74. a) H. Lachance, X. Lu, M. Gravel, D. G. Hall, J. Am. Chem. Soc. 2003, 125, 10 160-10 161;
75. b) V. Rauniyar, D.G. Hall, J. Am. Chem. Soc. 2004, 126, 4518-4519.
76. a) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118; Angew. Chem. Int. Ed. 1998, 37, 1986-2012, and references therein;
77. a) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118; Angew. Chem. Int. Ed. 1998, 37, 1986-2012, and references therein;
78. b) S. Itsuno in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 290-315, and references therein.
79. For examples, see: a) E. J. Corey, K. A. Cimprich, J. Am. Chem. Soc. 1994, 116, 3151-3152; b) N. N. Joshi, M. Srebnik, H. C. Brown, Tetrahedron Lett. 1989, 30, 5551-5554.
80. For examples, see: a) E. J. Corey, K. A. Cimprich, J. Am. Chem. Soc. 1994, 116, 3151-3152; b) N. N. Joshi, M. Srebnik, H. C. Brown, Tetrahedron Lett. 1989, 30, 5551-5554.
81. a) M. Kitamura, S. Suga, K. Kawai, R. Noyori, J. Am. Chem. Soc. 1986, 108, 6071-6072;
82. b) M. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028-4036;
83. for an excellent review of this topic, see: K. Soai, T. Shibata in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 911-922, and references therein.
84. P. J. Walsh, Acc. Chem. Res. 2003, 36, 739-749, and references therein.
85. B. L. Pagenkopf, E. M. Carreira, Tetrahedron Lett. 1998, 39, 9593-9596.
86. For a review, see: H. Ishibashi, K. Ishihara, H. Yamamoto, Chem. Rec. 2002, 2, 177-188.
87. a) S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8120-8130;
88. b) K. Ishihara, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 11 179-11 180;
89. c) K. Ishihara, S. Nakamura, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 12 854-12 855;
90. d) K. Ishihara, H. Nakamura, S. Nakamura, H. Yamamoto, J. Org. Chem. 1998, 63, 6444-6445;
91. e) K. Ishihara, D. Nakashima, Y. Hiraiwa, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 24-25.
92. a) S. Nakamura, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8131-8140;
93. b) K. Ishihara, S. Nakamura, H. Yamamoto, J. Am. Chem. Soc. 1999, 121, 4906-4907;
94. c) K. Ishihara, H. Ishibashi, H. Yamamoto, J. Am. Chem. Soc. 2002, 124, 3647-3655;
95. d) K. Ishihara, H. Ishibashi, H. Yamamoto, J. Am. Chem. Soc. 2001, 123, 1505-1506.
96. R. Davydov, T. Matsui, H. Fujii, M. Ikeda-Saito, B. M. Hoffman, J. Am. Chem. Soc. 2003, 125, 16 208-16 209.
97. For an excellent review, see: D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 1998, 110, 2092-2118; Angew. Chem. Int. Ed. 2001, 40, 92-138.
98. For an excellent review, see: D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 1998, 110, 2092-2118; Angew. Chem. Int. Ed. 2001, 40, 92-138.
99. a) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
100. b) A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846-5850.
101. Alternatively, the activation of carbonyl compounds by double hydrogen bonding was proposed; see: P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113; Angew. Chem. Int. Ed. 2004, 43, 2062-2064.
102. Alternatively, the activation of carbonyl compounds by double hydrogen bonding was proposed; see: P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113; Angew. Chem. Int. Ed. 2004, 43, 2062-2064.
103. N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12 094-12 095.