Nonreductive enantioselective ring opening of N-(methylsulfonyl)dicarboximides with diisopropoxytitanium α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanolate

Helvetica Chimica Acta

Volumn 79, Issue 3, 1996, Pages 875-894

  Ramón, Diego J ^a   Guillena, Gabriela ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000424872     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790328     Document Type: Article

References (68)

1. H. Hirschmann, in 'Comprehensive Biochemistry', Eds. M. Florkin and G. H. Stotz, Elsevier, New York, 1964, Vol. 12, p. 236.
2. a) D. Seebach, E. Hungerbühler, in 'Modern Synthetic Methods 1980', Ed. R. Scheffold, Salle and Sauerländer, Frankfurt/Aarau, 1980, p. 91;
3. b) P. Breuilles, T. Schmittberger, D. Uguen, Tetrahedron Lett. 1993, 34, 4205.
4. K. Mislow, J. Siegel, J Am. Chem. Soc. 1984, 106, 3319; S. Fujita, 'Symmetry and Combinatorial Enumeration in Chemistry', Springer-Verlag, Berlin, 1991.
5. K. Mislow, J. Siegel, J Am. Chem. Soc. 1984, 106, 3319; S. Fujita, 'Symmetry and Combinatorial Enumeration in Chemistry', Springer-Verlag, Berlin, 1991.
6. D. Seebach, Angew. Chem. 1990, 102, 1363; ibid. Int. Ed. 1990, 29, 1320.
7. D. Seebach, Angew. Chem. 1990, 102, 1363; ibid. Int. Ed. 1990, 29, 1320.
8. C. H. Wong, G. H. Whitesides, 'Enzymes in Synthetic Organic Chemistry', Eds. J. E. Baldwin and P. D. Magnus, Pergamon, Oxford, 1994; K. Drauz, H. Waldmann, 'Enzyme Catalysis in Organic Synthesis', VCH, Weinheim, 1995, Vol. 1 and 2.
9. C. H. Wong, G. H. Whitesides, 'Enzymes in Synthetic Organic Chemistry', Eds. J. E. Baldwin and P. D. Magnus, Pergamon, Oxford, 1994; K. Drauz, H. Waldmann, 'Enzyme Catalysis in Organic Synthesis', VCH, Weinheim, 1995, Vol. 1 and 2.
10. R. S. Ward, Chem Soc. Rev. 1990, 19, 1; W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; K. Mikami, S. Narisawa, M. Shimizu, M. Terada, ibid. 1992, 114, 6566; W. A. Nugent, R. L Harlow, ibid. 1994, 116, 6142; L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, ibid. 1995, 117, 5897.
11. R. S. Ward, Chem Soc. Rev. 1990, 19, 1; W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; K. Mikami, S. Narisawa, M. Shimizu, M. Terada, ibid. 1992, 114, 6566; W. A. Nugent, R. L Harlow, ibid. 1994, 116, 6142; L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, ibid. 1995, 117, 5897.
12. R. S. Ward, Chem Soc. Rev. 1990, 19, 1; W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; K. Mikami, S. Narisawa, M. Shimizu, M. Terada, ibid. 1992, 114, 6566; W. A. Nugent, R. L Harlow, ibid. 1994, 116, 6142; L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, ibid. 1995, 117, 5897.
13. R. S. Ward, Chem Soc. Rev. 1990, 19, 1; W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; K. Mikami, S. Narisawa, M. Shimizu, M. Terada, ibid. 1992, 114, 6566; W. A. Nugent, R. L Harlow, ibid. 1994, 116, 6142; L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, ibid. 1995, 117, 5897.
14. R. S. Ward, Chem Soc. Rev. 1990, 19, 1; W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768; K. Mikami, S. Narisawa, M. Shimizu, M. Terada, ibid. 1992, 114, 6566; W. A. Nugent, R. L Harlow, ibid. 1994, 116, 6142; L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, ibid. 1995, 117, 5897.
15. M. North, G. Zagotto, Synlett 1995, 639; H. Imado, T. Ishizuka, T. Kunieda, Tetrahedron Lett. 1995, 36, 931; R. S. Ward, A. Pelter, M. I. Edwards, J. Gilmore, Tetrahedron. Asymmetry 1995, 6, 843
16. M. North, G. Zagotto, Synlett 1995, 639; H. Imado, T. Ishizuka, T. Kunieda, Tetrahedron Lett. 1995, 36, 931; R. S. Ward, A. Pelter, M. I. Edwards, J. Gilmore, Tetrahedron. Asymmetry 1995, 6, 843
17. M. North, G. Zagotto, Synlett 1995, 639; H. Imado, T. Ishizuka, T. Kunieda, Tetrahedron Lett. 1995, 36, 931; R. S. Ward, A. Pelter, M. I. Edwards, J. Gilmore, Tetrahedron. Asymmetry 1995, 6, 843
18. a) K. Osakada, M. Obana, T. Ikariya, M. Saburi, S. Yoshikawa, Tetrahedron Lett. 1981, 22, 4297;
19. b) J. Hiratake, Y. Yamamoto, J. Oda, J. Chem. Soc., Chem. Commun. 1985, 1717;
20. c) S. A. Miller, A. R. Chamberlin, J. Am. Chem. Soc. 1990, 112, 8100;
21. d) K Matsuki, H. Inoue, M. Takeda, Tetrahedron Lett 1993, 34, 1167;
22. e) M Shimizu, K. Matsukawa, T. Fujisawa, Bull. Chem. Soc. Jpn. 1993, 66, 2128;
23. f) D. Seebach, G. Jaeschke, Y. M Wang, Angew. Chem. 1995, 107, 2605; ibid. Int. Ed. 1995, 34, 2395.
24. f) D. Seebach, G. Jaeschke, Y. M Wang, Angew. Chem. 1995, 107, 2605; ibid. Int. Ed. 1995, 34, 2395.
25. a) K. Matsuki, H. Inoue, A. Ishida, M. Takeda, Heterocycles 1993, 36, 937;
26. b) K. Matsuki, H. Inoue, A. Ishida, M. Takeda, M. Nakagawa, T. Hino, Chem. Pharm Bull. 1994, 42, 9;
27. c) R. Romagnoli, E. C. Roos, H. Hiemstra, M. J. Moolenaar, W. N. Speckamp, B. Kaptein, H. E. Schoemaker, Tetrahedron Lett. 1994, 35, 1087;
28. d) J. Kang, J. W. Lee, J. I. Kim, C. Pyun, ibid. 1995, 36, 4265.
29. D. Seebach, B Weidmann, L. Widler, in 'Modern Synthetic Methods 1983', Ed. R. Scheffold, Verlag Sauerländer, Aarau, 1983, p. 217.
30. W Oppolzer, P. Lienard, Helv. Chim. Acta 1992, 75, 2572.
31. T. W. Evans, W. M. Dehn, J. Am. Chem. Soc. 1929, 51, 3651
32. D. Seebach, D. A Plattner, A. K Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta 1992, 75, 2171.
33. A. K. Beck, B. Bastani, D. A. Plattner, W. Petter, D. Seebach, H. Braunschweiger, P. Gysi, L. La Vecchia, Chimia 1991, 45, 238.
34. Y. N. Ito, X. Ariza, A. K. Beck, A. Bohác, C Ganter, R. E Gawley, F N. M. Kühnle, J Tuleja, Y. M Wang, D. Seebach, Helv. Chim. Acta 1994, 77, 2071
35. D. Seebach, R. Dahinden, R E. Marti, A. K. Beck, D. A. Plattner, F. N. M Kühnle, J. Org. Chem. 1995, 60, 1788.
36. K. Narasaka, F. Kanai, M. Okudo, N. Miyoshi, Chem. Lett 1989, 1187.
37. M. Terada, K. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; D. Kitamoto, H. Imma, T. Nakai, Tetrahedron Lett 1995, 36, 1861.
38. M. Terada, K. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; D. Kitamoto, H. Imma, T. Nakai, Tetrahedron Lett 1995, 36, 1861.
39. T. Mukaiyama, A. Inubushi, S Suda, R Hara, S. Kobayashi, Chem. Lett. 1990, 1015.
40. M. Yoshioka, T. Kawakita, M. Ohno, Tetrahedron Lett. 1989, 30, 1657.
41. B. Schmidt, D. Seebach, Angew Chem. 1991, 103, 100; ibid Int Ed 1991, 30, 99; D. Seebach, A. K. Beck, B Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363.
42. B. Schmidt, D. Seebach, Angew Chem. 1991, 103, 100; ibid Int Ed 1991, 30, 99; D. Seebach, A. K. Beck, B Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363.
43. B. Schmidt, D. Seebach, Angew Chem. 1991, 103, 100; ibid Int Ed 1991, 30, 99; D. Seebach, A. K. Beck, B Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363.
44. R. Dahinden, R. E. Marti, T. Hintermann. ETH-Zürich, 1995, unpublished results.
45. E. H. Gold, E. Babad, J Org. Chem. 1972, 37, 2208.
46. N. Katagiri, M. Muto, C. Kaneko, Tetrahedron Lett. 1989, 30, 1645; C. F. Palmer, R. McCague, J. Chem. Soc., Perkin Trans. 1 1995, 1201; R. Csuk, P. Dörr, Tetrahedron 1995, 51, 5789.
47. N. Katagiri, M. Muto, C. Kaneko, Tetrahedron Lett. 1989, 30, 1645; C. F. Palmer, R. McCague, J. Chem. Soc., Perkin Trans. 1 1995, 1201; R. Csuk, P. Dörr, Tetrahedron 1995, 51, 5789.
48. N. Katagiri, M. Muto, C. Kaneko, Tetrahedron Lett. 1989, 30, 1645; C. F. Palmer, R. McCague, J. Chem. Soc., Perkin Trans. 1 1995, 1201; R. Csuk, P. Dörr, Tetrahedron 1995, 51, 5789.
49. H.-J. Gais, K. L. Lukas, A. Ball, S. Braun, H. J. Lindner, Liebigs Am. Chem. 1986, 687.
50. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512.
51. T. Kusumi, Y. Fujita, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2923; T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, ibid. 1991, 32, 2939; I. I. Ohtani, K. Hotta, Y. Ichikawa, M. Isobe, Chem. Lett. 1995, 513.
52. T. Kusumi, Y. Fujita, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2923; T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, ibid. 1991, 32, 2939; I. I. Ohtani, K. Hotta, Y. Ichikawa, M. Isobe, Chem. Lett. 1995, 513.
53. T. Kusumi, Y. Fujita, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2923; T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, ibid. 1991, 32, 2939; I. I. Ohtani, K. Hotta, Y. Ichikawa, M. Isobe, Chem. Lett. 1995, 513.
54. G. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143.
55. H. Schäfer, D. Seebach, Tetrahedron 1995, 51, 2305; D. J. Ramón, hitherto unpublished results.
56. H. Schäfer, D. Seebach, Tetrahedron 1995, 51, 2305; D. J. Ramón, hitherto unpublished results.
57. L. F. Tietze, C. Schneider, A. Montenbruck, Angew. Chem. 1994, 106, 1031; ibid. Int. Ed. 1994, 33, 980.
58. L. F. Tietze, C. Schneider, A. Montenbruck, Angew. Chem. 1994, 106, 1031; ibid. Int. Ed. 1994, 33, 980.
59. R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34; ibid. Int. Ed. 1991, 30, 49; M. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832.
60. R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34; ibid. Int. Ed. 1991, 30, 49; M. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832.
61. R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34; ibid. Int. Ed. 1991, 30, 49; M. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832.
62. D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, H. B. Kagan, J. Am. Chem. Soc. 1994, 116, 9430.
63. E. Wada, H. Pei, S. Kanemasa, Chem. Lett. 1994, 2345.
64. E. Wada, H. Yasouka, S. Kanemasa, Chem. Lett. 1994, 1637.
65. K. G. Bilyard, P. J. Garratt, R. Hunter, E. Lete, J. Org. Chem. 1982, 47, 4731.
66. G. C. Crockett, T. H. Koch, J. Org. Chem. 1977, 42, 2721.
67. M. S. Heller, A. M. Adelman, Synthesis 1970, 545.
68. G. M. Sheldrick, 'SHELXS-86, Program for the Solution of Crystal Structures', University of Göttingen, 1986.