Diastereo- and enantioselective synthesis of 1,2-amino alcohols and protected α-hydroxy aldehydes from glycol aldehyde hydrazones

Liebigs Annales

Volumn , Issue 1, 1996, Pages 11-26

  Enders, Dieter ^a   Reinhold, Ulrich ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Amino alcohols; Asymmetric synthesis; Electrophilic alkylation; Hydrazones; Nucleophilic 1,2 addition; Statin; Hydroxy aldehydes

Indexed keywords

EID: 0001850963     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960104     Document Type: Article

References (84)

1. Recent reviews on the synthesis and application of 1,2-amino alcohols: [1a] R. Henning, Nachr. Chem. Techn. Lab. 1990, 38, 460-464.
2. [1b] M. T. Reetz, Angew. Chem. 1991, 103, 1559-1573;
3. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1545.
4. [1c] J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, p. 365.
5. [1d] Y. Ohfune, Acc. Chem. Res. 1992, 25, 360-366.
6. [1f] T. Yokomatsu, Y. Yuasa, S. Shibuya, Heterocycles 1992, 33, 1051-1078.
7. [1g] A. Golebiowski, J. Jurczak, Synlett 1993, 241-245.
8. [1h] T. Kunieda, T. Ishizuka in Studies in Natural Products Chemistry, Vol. 12 (Ed.: Atta-ur-Rahman), Elsevier, New York, 1993, p. 411.
9. Review articles: [2a] D. H. Rich in Comprehensive Medicinal Chemistry, Vol. 2 (Ed.: C. Hansch, P. G. Sammes, J. B. Taylor), Pergamon, 1990, p. 391.
10. [2b] J. Gante, Angew. Chem. 1994, 106, 1780-1802;
11. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720.
12. [3a] H. Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki, M. Hamada, T. Takeuchi, J. Antibiot. 1970, 23, 259-265.
13. [3b] H. Morishima, T. Takita, T. Aoyagi, T. Takeuchi, H. Umezawa, J. Antibiot. ibid 1970, 23, 263-265.
14. [4a] D. H. Rich, E. T. Sun, J. Med. Chem. 1980, 23, 27-33.
15. [4b] S. Omura, N. Imamura, K. Kawakita, Y. Mori, Y. Yamazaki, R. Masuma, Y. Takahachi, H. Tanaka, L.-Y. Huang, H. B. Woodruff, J. Antibiot. 1986, 39, 1079-1085.
16. Recent asymmetric syntheses: [5a] D. Enders, U. Jegelka, B. Dücker, Angew. Chem. 1993, 105, 423-425;
17. Angew. Chem. Int. Ed. Engl. 1993, 32, 423-425.
18. [5b] S. Kanemasa, T. Mori, A. Tasukawa, Tetrahedron Lett. 1993, 34, 8293-8296.
19. [5c] A. G. M. Barrett, M. A. Seefeld, Tetrahedron 1993, 49, 7857-7870.
20. [5d] K. Hattori, H. Yamamoto, Tetrahedron ibid 1994, 50, 2785-2792.
21. [5e] M. E. Bunnage, A. J. Burke, S. G. Davies, C. J. Goodwin, Tetrahedron: Asymmetry 1994, 5, 203-206.
22. [5f] A. M. Kanezawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
23. [5g] P. Besse, H. Veschambre, R. Chênevert, M. Dickman, Tetrahedron: Asymmetry 1994, 5, 1727-1744.
24. [5h] S. Matsubara, H. Ukita, T. Kodama, K. Utimoto, Chem. Lett. 1994, 831-834.
25. [5i] O. Lingibe, B. Graffe, M.-C. Sacquet, G. Lhommet, Heterocycles 1994, 37, 1469-1472.
26. [5j] Z. Shi, G. Lin, Tetrahedron 1995, 51, 2427-2434.
27. [5k] D. Enders, D. L. Whitehouse, J. Runsink, Chem. Eur. J. 1995, 1, 382-388.
28. asymmetric syntheses of statin: [5l] T. Ishizuka, S. Ishibuchi, T. Kunieda, Tetrahedron 1993, 49, 1841-1852.
29. [5m] L. Bertelli, R. Fiaschi, E. Napolitano, Gazz. Chim. Ital. 1993, 123, 521-524.
30. [5n] R. M. Williams, P. J. Colson, W. Zhai, Tetrahedron Lett. 1994, 35, 9371-9374.
31. For some leading references on α-hydroxy aldehydes see: [6a] D. A. Evans, J. V. Nelson, T. R. Taber in Top. Stereochem., Vol. 13 (Eds.: N. L. Allinger, E. L. Eliel, S. H. Wilen), J. Wiley, New York, 1983, 13, p. 1.
32. [6b] C. H. Heathcock in Asymmetric Synthesis, Vol. 3B (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 111.
33. [6c] M. T. Reetz, Angew. Chem. 1984, 96, 542-555;
34. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
35. [6d] J. Jurczak, S. Pikul, T. Bauer, Tetrahedron 1986, 42, 447-488.
36. [6e] D. Enders, V. Bhushan, Tetrahedron Lett. 1988, 29, 2437-2440 and literatur cited therein.
37. For asymmetric Syntheses of α-hydroxy ketones see: [6f] B. B. Lohray, D. Enders, Helv. Chim. Acta 1989, 72, 980-984.
38. [6g] D. Enders, B. Bockstiegel, Synthesis 1989, 493-496.
39. [6h] D. Enders, W. Gatzweiler, U. Jegelka, Synthesis ibid 1991, 1137-1141.
40. [6i] D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453-2456.
41. [6j] D. Enders, D. Backhaus, Synlett 1995, 631-632.
42. [7a] D. Enders, U. Reinhold, Synlett 1994, 792-794;
43. an overview of stereoselective syntheses of α-hydroxy aldehydes is given therein. Recent asymmetric syntheses of α-hydroxy aldehydes: [7b] J. Peters, T. Zelinski, T. Minuth, M.-R. Kula, Tetrahedron: Asymmetry 1993, 4, 1683-1692.
44. [7c] I. Ferraboschi, E. Santaniello, M. Tingoli, F. Argozzini, F. Molinari, Tetrahedron: Asymmetry 1993, 4, 1931-1940.
45. [7d] I. Henderson, K. B. Sharpless, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 558-561.
46. D. Enders, U. Reinhold, Angew. Chem. 1995, 107, 1332-1334;
47. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222.
48. Reviews on SAMP/RAMP hydrazone method: [9a] D. Enders in Asymmetric Synthesis, Vol. 3B (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275.
49. [9b] D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-202.
50. [9c] D. Enders, M. Klatt in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, New York, 1995, in press.
51. D. Enders, H. Kipphardt, P. Gerdes, L. J. Breña-Valle, V. Bhushan, Bull. Soc. Chim. Belg. 1988, 97, 691-704.
52. T. Cuvigny, J.-F. Le Borgne, M. Larchevêque, H. Normant, Synthesis 1976, 237.
53. [12a] D. Enders, G. Bachstädter, K. A. M. Kremer, M. Marsch, K. Harms, G. Boche, Angew. Chem. 1988, 100, 1580-1581;
54. Angew. Chem., Int. Ed. Engl. 1988, 27, 1522-1523.
55. [12b] D. Enders, Chem. Scripta 1985, 25, 139-147.
56. [13a] D. Enders, A. Plant, D. Backhaus, U. Reinhold, Tetrahedron 1995, 51, 10699-10714.
57. [13b] D. Enders, A. Plant, Synlett 1994, 1054-1056.
58. [13c] D. Enders, D. Backhaus, J. Runsink, Angew. Chem. 1994, 106, 2167-2170;
59. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098-2100.
60. [13d] R. Fernández, C. Gasch, J.-M. Lassaletta, J.-M. Ilera, Tetrahedron Lett. 1994, 35, 471-474.
61. [14a] D. Parker, Chem. Rev. 1991, 91, 1441-1457.
62. [14b] H. Hiemstra, H. Wynberg, Tetrahedron Lett. 1977, 16, 2183-2186.
63. [14c] T. Tsunoda, M. Suzuki, R. Noyori, R. Tetrahedron Lett. ibid. 1980, 21, 1357-1358.
64. T. W. Greene, P. G. M. Wuts in Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991.
65. [16a] A. Alexakis, N. Lensen, J.-P. Tranchier, P. Mangeney, J. Org. Chem. 1992, 57, 4563-4565.
66. [16b] Lower inductions were achieved for the 1,2-addition of Grignard reagents in toluene to hydrazone 2c, d in comparison with organolithium compounds (de < 90%).
67. [16c] D. Enders, J. Schankat, M. Klatt, Synlett 1994, 795-798 and literature cited therein.
68. [17a] C. Nübling, Dissertation, RWTH Aachen, 1987.
69. [17b] S. E. Denmark, O. Nicaise, J. P. Edwards, J. Org. Chem. 1990, 55, 6219-6223.
70. [18a] D. A. Claremon, P. K. Lumma, B. T. Philips, J. Am. Chem. Soc. 1986, 108, 8265-8266.
71. [18b] W. R. Baker, S. L. Condon, J. Org. Chem. 1993, 58, 3277-3284.
72. [19a] J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549.
73. [19b] J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
74. J. A. Marshall, A. W. Garofalo, J. Org. Chem. 1993, 58, 3675-3680.
75. [21a] R. Steulmann, H. Klostermeyer, Liebigs Ann. Chem. 1975, 2245-2250.
76. [21b] W.-S. Liu, S. C. Smith, G. I. Glover, J. Med. Chem. 1979, 22, 577-579.
77. [22a] L. F. Hatch, S. S. Nesbit, J. Am. Chem. Soc. 1945, 67, 39-41.
78. [22b] S. K. Massad, L. D. Hawkins, D. C. Baker, J. Org. Chem. 1983, 48, 5180-5182.
79. [22c] L. Banfi, A. Bernadi, C. Gennari, C. Scolastico, J. Org. Chem. 1984, 49, 3784-3790.
80. [22d] C. C. Sweeley, R. Bentley, M. Makita, W. W. Wells, J. Am. Chem. Soc. 1963, 85, 2497-2507.
81. [23a] K. Takai, C. H. Heathcock, J. Org. Chem. 1985, 50, 3247-3251.
82. [23b] R. Bernardi, C. Fuganti, P. Grasselli, Tetrahedron Lett. 1981, 22, 4021-4024.
83. [23c] A.-M. Matre, G. Mousset, R. B. Rhlid, H. Veschambre, Tetrahedron Lett. 1990, 31, 2599-2602.
84. [23d] S. Fernández, R. Brieva, F. Rebolledo, V. Gotor, J. Chem. Soc., Perkin Trans. I, 1992, 2885-2889.