Enantiośelective synthesis of vicinal amino alcohols by oxa-michael addition of (-)-N-formylnorephedrine to nitroalkenes

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 20, 1996, Pages 2388-2390

  Enders, Dieter ^a   Haertwig, Andreas ^a   Raabe, Gerhard ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Amino alcohols; Asymmetric syntheses; Michael additions; Nitroalkenes; Synthetic methods

Indexed keywords

EID: 0030472295     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623881     Document Type: Article

References (79)

1. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
2. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
3. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
4. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
5. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
6. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
7. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
8. Reviews: a) R. Henning, Nachr. Chem. Tech. Lab. 1990, 38, 460-464; b) K. Tomioka, Synthesis 1990, 541-549; c) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69; d) Y. Ohfune, Ace. Chem. Res. 1992, 25, 360-366; e) A. Golebiowski, J. Jurezak, Synlett 1993, 241 -245; f) T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York 1993, pp. 411 -444; g) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
9. a) H. Sasai, N. Itoh, T. Suzuki, M. Shibasaki, Tetrahedron Lett. 1993, 34, 855-858;
10. b) H. Sasai, T. Suzuki, N. Itoh, S. Arai, M. Shibasaki, ibid. 1993, 34, 2657-2660;
11. c) R. Chinchilla, C. Nájera, P. Sánchez-Agulló, Tetrahedron: Asymmetry 1994, 5, 1393-1402;
12. d) N. Kise, N. Inakoshi. Y. Matsumura, Tetrahedron Lett. 1995, 36, 909-912;
13. e) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388-7389;
14. f) R. E. Marti, J. Heinzer, D. Seebach, Liebigs Ann. 1995, 1193-1215;
15. g) D. Enders, U. Reinhold, ibid. 1996, 11-26;
16. h) Angew. Chem. 1995, 107, 1332-1334; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219-1222;
17. h) Angew. Chem. 1995, 107, 1332-1334; Angew. Chem. Int. Ed. Engl. 1995, 34, 1219-1222;
18. i) T. Wirth, ibid 1996, 108, 65-67 and 1996, 35, 61-63 and references therein.
19. i) T. Wirth, ibid 1996, 108, 65-67 and 1996, 35, 61-63 and references therein.
20. a) J. M. Klunder, S. Y. Ko, K. B. Sharpless, J. Org. Chem. 1986, 51, 3710-3712;
21. b) M. Brunner, L. Mussmann, D. Vogt, Synlett 1993, 893-894;
22. c) C. E. Harris, G. B. Fischer, D. Beardsley, L. Lee, C. T. Goralski, L. W. Nicholson, B. Singaram, J. Org. Chem. 1994, 59, 7746-7751;
23. d) H.-T. Chang, K. B. Sharpless, Tetrahedron Lett. 1996, 37, 3219-3222,
24. e) J. L. Leighton, E. N. Jacobsen, J. Org. Chem. 1996, 61, 389-390,
25. f) C. H. Senanayake, R. D. Larsen, L. M. DiMichele, J. Liu, P. H. Toma, R. G. Ball, T. R. Verhoeven, P. J. Reider, Tetrahedron: Asymmetry 1996, 7, 1501-1506.
26. G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 103, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
27. G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 103, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
28. a) C. T. Goralski, D. L. Hasha, L. W. Nicholson, D. Zakett, G. B. Fischer, B. Singaram, Tetrahedron Lett. 1994, 35, 3251-3254;
29. b) G. B. Fischer, C. T. Goralski, L. W. Nicholson, D. L. Hasha, D. Zakett, B. Singaram, J. Org. Chem. 1995, 60, 2026-2034.
30. Overview of oxa-Michael addition to nitroalkenes: V. V. Perealkin, E. S. Lipina, V. M. Berestovitskaya, D. A. Efremov, Nitroalkenes, Wiley, Chichester, 1994, pp. 67-73 and references therein.
31. a) J. R. Hwu, N. Wang, J. Chem. Soc. Chem. Commun. 1987, 427-428;
32. b) J. M. Aizpurua, M. Oiarbide, C. Palomo, Tetrahedron Lett. 1987, 28, 5361-5364;
33. c) A. Kamimura, N. Ono, ibid. 1989, 30, 731-734;
34. d) A. Kamimura, H. Sasatani, T. Hashimoto, T. Kawai, K. Hori, N. Ono, J Org. Chem. 1990, 55, 2437-2442;
35. e) A. G. M. Barrett, S. A. Lebold, ibid. 1990, 55, 3853-3857;
36. f) K. Hori, S. Higuchi, A. Kamimura, ibid. 1990, 55, 5900-5905;
37. g) A. G. M. Barrett, P. D. Weipert, D. Dhanak, R. K. Husa, S. A. Lebold, J. Am. Chem. Soc. 1991, 113, 9820-9824;
38. h) A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127;
39. i) J. L. Duffy, J. A. Kurth, M. J. Kurth, Tetrahedron Lett. 1993, 34, 1259-1260;
40. j) N. Garg, N. Hossain, J. Chattopadhyaya, Tetrahedron 1994, 50, 5273-5278;
41. k) A. G. M. Barrett, D. J. Rys, J. Chem. Soc. Perkin Trans, 1 1995, 1009-1017.
42. F. Loydl, Justus Liebigs Ann. C 1878, 192, 80-89.
43. a) T. Purdie, Ber. Dtsch. Chem. Ges. 1881, 14, 2238;
44. b) L. Claisen, L. Crismer, Justus Liebigs Ann. C 1883, 218, 129-144;
45. c) C. Liebermann, Ber. Dtsch. Chem. Ges. 1893, 26, 1876-1879;
46. d) C. F. Koelsch, J. Am. Chem. Soc. 1943, 65, 437-439.
47. Overview of oxa-Michael addition: A. Berkessel, Methods of Organic Chemistry (Houben-Weyl) 4th ed. 1952-, Vol. E21e 1995, pp. 4818-4856 and references therein.
48. a) S. Thaisrivongs, D. Seebach, J. Am. Chem. Soc. 1983, 105, 7407-7413;
49. b) J. Mulzer, M. Kappert, G. Huttner, I. Jibril, Angew. Chem. 1984, 96, 726-727; Angew. Chem. Int. Ed. Engl. 1984, 23, 704-705;
50. b) J. Mulzer, M. Kappert, G. Huttner, I. Jibril, Angew. Chem. 1984, 96, 726-727; Angew. Chem. Int. Ed. Engl. 1984, 23, 704-705;
51. c) A. Bernardi, S. Cardani, C. Scolastico, R. Villa, Tetrahedron 1990, 46, 1987-1998;
52. d) S. Cardani, C. Scolastico, R. Villa, ibid. 1990, 46, 7283-7288;
53. e) A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 1994, 116, 3324-3336;
54. f) T. Hosokawa, T. Yamanaka, M. Itotani, S.-I. Murahashi, J. Org. Chem. 1995, 60, 6159-6167.
55. a) T. Kitazume, T. Ikeya, K. Murata, J. Chem. Soc., Chem. Commun. 1986, 1331-1333;
56. b) M. A. Findeis, G. M. Whitesides, J. Org. Chem. 1987, 52, 2838-2848.
57. a) S. S. Ko, L. L. Klein, K.-P. Pfaff, Y. Kishi, Tetrahedron Lett. 1982, 23, 4415-4418;
58. b) C. Iwata, K. Hattori, S. Uchida, T. Imanishi, ibid. 1984, 25, 2995-2998;
59. c) B. D. Roth, W. H. Roark, ibid. 1988, 29, 1255-1258;
60. d) K. C. Nicolaou, C.-K. Hwang, M. E. Duggan, J. Am. Chem. Soc. 1989, 111, 6682-6690;
61. e) V. S. Martin, M. T. Nuñez, M. A. Ramirez, M. A. Soler, Tetrahedron Lett. 1990, 31, 763-766;
62. f) T. Mandai, M. Ueda, K. Kashiwagi, M. Kawada, J. Tsuji, ibid. 1993, 34, 111-114;
63. g) J. M. Palazón, M. A. Soler, M. A. Ramirez, V. S. Martin, ibid. 1993, 34, 5467-5470;
64. h) M. A. Soler, J. M. Palazón, V. S. Martin, ibid. 1993, 34, 5471-5474;
65. i) D. A. Evans, J. A. Gauchet-Prunet, J. Org. Chem. 1993, 58, 2446-2453;
66. j) S. D. Burke, K. W. Jung, J. R. Phillips, R. E. Perri, Tetrahedron Lett. 1994, 35, 703-706.
67. The spectroscopic data of the auxiliary are identical with those found in the literature: a) I. A. Al-Meshal, M. Nasir, F. S. El-Feraly, Phytochemistry 1986, 25, 2241-2242; b) B. D. Berrang, A. H. Lewin, F. I. Carroll, J. Org. Chem. 1982, 47, 2643-2647; c) R. Vilvala, T. Haapanen, Acta Pharm. Fenn. 1980, 89, 253-257.
68. The spectroscopic data of the auxiliary are identical with those found in the literature: a) I. A. Al-Meshal, M. Nasir, F. S. El-Feraly, Phytochemistry 1986, 25, 2241-2242; b) B. D. Berrang, A. H. Lewin, F. I. Carroll, J. Org. Chem. 1982, 47, 2643-2647; c) R. Vilvala, T. Haapanen, Acta Pharm. Fenn. 1980, 89, 253-257.
69. The spectroscopic data of the auxiliary are identical with those found in the literature: a) I. A. Al-Meshal, M. Nasir, F. S. El-Feraly, Phytochemistry 1986, 25, 2241-2242; b) B. D. Berrang, A. H. Lewin, F. I. Carroll, J. Org. Chem. 1982, 47, 2643-2647; c) R. Vilvala, T. Haapanen, Acta Pharm. Fenn. 1980, 89, 253-257.
70. -3. The configuration of C2 was obtained by using the known configuration of C3 and C4. Crystallographic data (excluding structure factors) for the structure(s) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-91. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223) 336-033; e-mail: teched@chemerys.cam.ac.uk).
71. S. R. Hall, H. D. Flack, J. M. Stewart XTAL3.2 Reference Manual, Universities of Western Australia, Geneva, and Maryland, Lamb, Perth 1992.
72. E. Keller, Chem. Unserer Zeit 1986, 20, 178-181.
73. a) M. Petrini, R. Ballini, G. Rosini, Synthesis 1987, 713-714;
74. b) A. S. Kende, J. S. Mendoza, Tetrahedron Lett. 1991, 32, 1699-1702.
75. L. F. Tietze, A. Dölle, K. Schiemann, Angew. Chem. 1992, 104, 1366-1367; Angew. Chem. Int. Ed. Engl. 1992, 31, 1372-1373.
76. L. F. Tietze, A. Dölle, K. Schiemann, Angew. Chem. 1992, 104, 1366-1367; Angew. Chem. Int. Ed. Engl. 1992, 31, 1372-1373.
77. a) J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549;
78. b) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
79. All new compounds gave appropriate spectroscopic data (1R, NMR, MS) and correct elemental analyses.