Direct catalytic enantioselective α-aminoxylation of ketones: A stereoselective synthesis of α-hydroxy and α,α′- dihydroxy ketones

Angewandte Chemie - International Edition

Volumn 43, Issue 9, 2004, Pages 1109-1112

  Bøgevig, Anders ^a   Sundén, Henrik ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Asymmetric catalysis; Ketones; Oxidation; Proline

Indexed keywords

CARBONYLATION; CATALYSIS; SYNTHESIS (CHEMICAL);

AMINOXYLATION; CHIRAL; ENANTIOSELECTIVITIES; NITROSOBENZENE;

KETONES;

CARBONYL DERIVATIVE; KETONE DERIVATIVE; NITROSOBENZENE;

ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1842792133     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353018     Document Type: Article

References (89)

1. a) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999;
2. b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
3. c) Catalytic Asymmetric Synthesis, 2nd ed (Ed.: I. Ojima, Wiley-VCH, New York, 2000.
4. F. A. Davis, B. C. Chen in Houben-Weyl: Methods of Organic Chemistry, Vol. E21 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme, Stuttgart, 1995, p. 4497.
5. F. A. Davis, B. C. Chen, Chem. Rev. 1992, 92, 919, and references therein.
6. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6038.
7. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
8. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
9. b) B. List, Tetrahedron 2002, 58, 5573;
10. c) J. Gröger, J. Wilken, Angew. Chem. 2001, 113, 545; Angew. Chem. Int. Ed. 2001, 40, 529;
11. c) J. Gröger, J. Wilken, Angew. Chem. 2001, 113, 545; Angew. Chem. Int. Ed. 2001, 40, 529;
12. d) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481;
13. e) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975.
14. e) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975.
15. a) "Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds": Z. G. Hajos, D. R. Parrish, German patent DE 2102623, July 29, 1971;
16. b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615;
17. c) "Optically Active 1,5-Indanone and 1,6-Naphthalenedionene": U. Eder, G. Sauer, R. Wiechert, German patent DE2014757, October 7, 1971;
18. d) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496;
19. d) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496;
20. e) C. Agami, Bull. Soc. Chim. Fr. 1988, 499.
21. For example, the total synthesis of taxol: S. J. Danishefsky, J. Am. Chem. Soc. 1996, 118, 2843.
22. For aldol reactions, see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395;
23. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386;
24. c) K. Saktihvel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
25. d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301;
26. e) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573;
27. f) A. Córdova, W. Notz, C. F. Barbas III, Chem. Commun. 2002, 67, 3034;
28. g) A. Bøgevig, K. Juhl, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620;
29. h) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798;
30. i) N. S. Chowdari, D. B. Ramachary, A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591;
31. j) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891; Angew. Chem. Int. Ed. 2003, 42, 2785;
32. j) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891; Angew. Chem. Int. Ed. 2003, 42, 2785;
33. k) Z. Tang, F. Jiang, L.-T. Yu, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, J. Am. Chem. Soc. 2003, 125, 5262.
34. For Mannich reaction, see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
35. b) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1844;
36. c) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866;
37. d) A. Córdova, Synlett 2003, 1651;
38. e) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 7749;
39. f) S.-i. Watanabe, A. Córdova, F. Tanaka, C. F. Barbas III, Org. lett. 2002, 4, 4519;
40. g) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923;
41. h) B. List, P. Porjalev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
42. i) W. Notz, K. Sakthivel, T. Bui, G. Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199;
43. j) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677;
44. j) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805; Angew. Chem. Int. Ed. 2003, 42, 3677;
45. k) E. N. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964.
46. For α-aminations, see: a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868; Angew. Chem. Int. Ed. 2002, 41, 1790;
47. For α-aminations, see: a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868; Angew. Chem. Int. Ed. 2002, 41, 1790;
48. b) B. List, J. Am. Chem. Soc. 2002, 124, 5656;
49. c) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254.
50. For Michael reactions, see: a) B. List, H. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423;
51. b) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520;
52. b) M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shiraishi, M. Hirama, Tetrahedron 1997, 53, 11223;
53. c) M. Yamaguchi, Y. Igarashi, T. Shiraishi, M. Hirama, Tetrahedron Lett. 1994, 35, 8233;
54. d) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975;
55. e) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441;
56. f) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737;
57. g) D. J. Hortsmann, D. J. Guerin, S. J. Miller, Angew. Chem. 2000, 112, 3781; Angew. Chem. Int. Ed. 2000, 39, 3635;
58. g) D. J. Hortsmann, D. J. Guerin, S. J. Miller, Angew. Chem. 2000, 112, 3781; Angew. Chem. Int. Ed. 2000, 39, 3635;
59. h) A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611;
60. i) D. J. Guerin, S. J. Miller, J. Am. Chem. Soc. 2002, 124, 2134;
61. j) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685; Angew. Chem. Int. Ed. 2003, 42, 661;
62. j) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685; Angew. Chem. Int. Ed. 2003, 42, 661;
63. j) N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331;
64. k) O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559;
65. l) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105; Angew. Chem. Int. Ed. 2003, 42, 4955;
66. l) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105; Angew. Chem. Int. Ed. 2003, 42, 4955;
67. m) D. Enders, A. Seki, Synlett 2002, 26.
68. For Diels-Alder reactions, see: a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
69. b) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
70. for hetero-Diels-Alder reactions, see: d) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498;
71. for hetero-Diels-Alder reactions, see: d) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498;
72. e) Y. Huang, K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.
73. For alkylation of electron-rich benzene systems, see: a) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370;
74. b) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
75. c) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894.
76. For 1,3-dipolar cycloadditions, see: a) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874;
77. b) S. Karlsson, H. Högberg, Tetrahedron: Asymmetry 2002, 13, 923.
78. For an example of a Strecker reaction, see: P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012.
79. For other reactions, see: a) A. E. Taggi, A. M. Hafez, H. Wack, B. Young, W. J. Drury III, T. Lectka, J. Am. Chem. Soc. 2000, 122, 7831;
80. b) B. R. Sculimbrene, A. J. Morgan, S. J. Miller, J. Am. Chem. Soc. 2002, 124, 11653;
81. c) M. Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058.
82. During the preparation of this manuscript two excellent independent reports of proline-catalyzed ct-oxidations of aldehydes were reported, see: a) G. Zhong, Angew. Chem. 2003,115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
83. During the preparation of this manuscript two excellent independent reports of proline-catalyzed ct-oxidations of aldehydes were reported, see: a) G. Zhong, Angew. Chem. 2003,115, 4379; Angew. Chem. Int. Ed. 2003, 42, 4247;
84. b) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808.
85. The α-oxy aniline adducts racemize and decompose upon storage in solution and at room temperature and should therefore be stored as solids at 4 °C or reduced to the more stable corresponding monoprotected diols.
86. 3).[4]
87. S. Bahmanyar, K. N. Houk, Org. Lett. 2003, 5, 1249, and references therein.
88. Note added in proof (19.1.2004): Please see the following communication by Hayashi et al., which describes related chemistry: Y. Hayashi, J. Yamaguchi, T. Suniya, M. Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed. 2004, 43, 1112.
89. Note added in proof (19.1.2004): Please see the following communication by Hayashi et al., which describes related chemistry: Y. Hayashi, J. Yamaguchi, T. Suniya, M. Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed. 2004, 43, 1112.