Synthesis of enantiopure homoallylic alcohols and ethers by diastereoselective allylation of aldehydes

Chemistry - A European Journal

Volumn 2, Issue 9, 1996, Pages 1164-1172

  Tietze, Lutz F ^a   Schiemann, Kai ^a   Wegner, Christoph ^a   Wulff, Christian ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Allylations; Allylsilanes; Double stereodifferentiation; Ephedrine; Homoallylic alcohols

Indexed keywords

ALDEHYDES; ALLYLATION; AMMONIA; LIQUEFIED GASES; STEREOSELECTIVITY;

ALLYLATIONS; ALLYLSILANES; EPHEDRINE; HOMOALLYLIC ALCOHOL; STEREODIFFERENTIATION;

ETHERS;

EID: 0001060158     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020920     Document Type: Article

References (60)

1. Reviews: Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
2. W. R. Roush in Comprehensive Organic Synthesis, Vol. 2 (Ed.: C. H. Heathcock), Pergamon, Oxford, 1991, p. 1.
3. a) R. W. Hoffmann, U. Weidmann, Chem. Ber. 1985, 118, 3966.
4. b) R. W. Hoffmann, T. Herold, ibid. 1981, 114, 375.
5. c) H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092.
6. d) H. C. Brown, K. S. Bhat, ibid. 1986, 108, 293.
7. e) H. C. Brown, P. K. Jadhav, K. S. Bhat, ibid. 1988, 110, 1535.
8. f) H. C. Brown, P. K. Jadhav, J. Org. Chem. 1984, 49, 4089.
9. g) H. C. Brown, R. S. Randad, K. S. Bhat, M. Zaidlewicz, U. S. Racherla, J. Am. Chem. Soc. 1990, 112, 2389.
10. h) U.S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401.
11. i) H. C. Brown, U. S. Racherla, Y. Liao, V. V. Khanna, ibid. 1992, 57, 6608.
12. j) J. Garcia, B. M. Kim, S. Masamune, ibid. 1987, 52, 4831.
13. k) R. P. Short, S. Masamune, J. Am. Chem. Soc. 1989, 111, 1892.
14. l) W. R. Roush, A. E. Walts, L. K. Hoong, ibid. 1985, 107, 8186.
15. m) W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, R. L. Halterman, ibid. 1990, 112, 6339.
16. n) W. R. Roush, K. Ando, L. Banfi, ibid. 1988, 110, 3979.
17. o) E. J. Corey, C. M. Yu, S. S. Kim, ibid. 1989, 111, 5495.
18. p) K. Ditrich, T. Bube, R. Stürmer, R. W. Hoffmann, Angew. Chem. 1986, 98, 1016;
19. Angew. Chem. Int. Ed. Engl. 1986, 25, 1028.
20. a) M. T. Reetz, T. Zierke, Chem. Ind. 1988, 663.
21. b) Review: R. O. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807.
22. c) A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321.
23. a) D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448.
24. b) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1991, 113, 8089.
25. c) W. S. Johnson, J. D. Elliot, ibid. 1983, 105, 2088.
26. d) J. M. McNamara, Y. Kishi, ibid. 1982, 104, 7371.
27. e) H. G. Howell, P. R. Brodfuehrer, C. Sapino, J. Org. Chem. 1985, 50, 2598.
28. f) S. F. Martin, C. Gluchowsky, C. L. Campbell, R. C. Chapman, ibid. 1984, 49, 2513.
29. g) D. Seebach, R. Imwinkelried, G. Stucky, Angew. Chem. 1986, 98, 182;
30. Angew. Chem. Int. Ed. Engl. 1986, 25, 178.
31. h) A. Mekhalfia, I. E. Markó, Tetrahedron Lett. 1991, 32, 4779.
32. a) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001,
33. b) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467.
34. c) K. Ishihara, M. Mouri, Q, Gao, T. Maruyama, K. Furuta, H. Yamamoto, ibid. 1993, 115, 11490.
35. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137;
36. Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
37. A short communication of the work has already appeared: L. F. Tietze, A. Dölle, K. Schiemann, Angew. Chem. 1992, 104, 1366;
38. Angew. Chem. Int. Ed. Engl. 1992, 31, 1372.
39. L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851.
40. A. P. Davis, M. Jaspars, Angew. Chem. 1992, 104, 475;
41. Angew. Chem. Int. Ed. Engl. 1992, 31, 470.
42. a) D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448.
43. b) W. S. Johnson, P. H. Crackett, J. D. Elliott. J. J. Jasodzinski, S. D. Lindell, S. Natarajan, Tetrahedron Lett. 1984, 25, 3951.
44. D. Sames, Y. Liu, L. DeYoung, R. Polt, J. Org. Chem. 1995, 60, 2153.
45. J. L. Broeker, R. W. Hoffmann,K. N. Houk, J. Am. Chem. Soc. 1991, 113, 5006.
46. It has been shown that chiral acetals are excellent elements for stereocontrol: a) A. Alexakis, P. Mangeney, Tetrahedron: Asymmetry 1990, 1, 477.
47. b) S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1991, 113, 8089.
48. c) S. E. Denmark, N. G. Almstead, J. Org. Chem. 1991, 56, 6458.
49. d) ibid. 1991, 56, 6485.
50. e) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, C. H. Heathcock, ibid. 1990, 55, 6107.
51. f) C. Agami, F. Couty, C. Lequesne, Tetrahedron Lett. 1994, 35, 3309.
52. g) G. Poli, E. Maccagni, L. Manzoni, T. Pilati, C. Scolastico, Synlett 1995, 71.
53. h) H. Pellissier, R. Faure, M. Santelli, J. Chem. Soc. Chem. Commun. 1995, 1847.
54. i) L. Colombo, M. Di Giacomo, G. Brusotti, G. Delogu, Tetrahedron Lett. 1994, 35, 2063.
55. j) K. C. Frieboes, T. Harder, D. Aulbert, C. Strahringer, M. Bolte, D. Hoppe, Synlett 1993, 921.
56. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1;
57. Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
58. C. Djerassi, L. E. Geller, J. Am. Chem. Soc. 1959, 81, 2789.
59. H. S. Forrest, J. Walker, J. Chem. Soc. 1949, 2002.
60. R. W. Hoffmann, A. Schlapbach, Tetrahedron 1992, 48, 1959.