3,3'-Dinitro-octahydrobinaphthol: A new chiral ligand for metal-catalyzed enantioselective reactions

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5273-5276

  Reetz, Manfred T ^a   Merk, Claudia ^a   Naberfeld, Guido ^a   Rudolph, Joachim ^a   Griebenow, Nils ^a   Goddard, Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; METAL; NAPHTHOL DERIVATIVE; TITANIUM;

ARTICLE; CRYSTAL STRUCTURE; ENANTIOMER; OXIDATION; STEREOCHEMISTRY;

EID: 0030805613     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01149-0     Document Type: Article

References (37)

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6. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
7. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
8. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
9. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
10. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
11. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671; Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967; Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. (Cambridge) 1997, 281; see also: Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. 1996, 108, 2521; Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
12. Reviews of chiral Lewis acids: Narasaka, K. Synthesis 1991, 1; Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; p 413.
13. Reviews of chiral Lewis acids: Narasaka, K. Synthesis 1991, 1; Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; p 413.
14. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
15. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
16. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
17. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
18. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
19. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
20. See for example: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264; Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938; Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083; Kaufmann, D.; Boese, R. Angew. Chem. 1990, 702, 568; Angew. Chem., Int. Ed. Engl. 1990, 29, 545; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897; Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
21. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194; Shibasaki, M.; Sasai, H. Pure Appl. Chem. 1996, 68, 523.
22. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194; Shibasaki, M.; Sasai, H. Pure Appl. Chem. 1996, 68, 523.
23. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
24. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
25. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
26. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
27. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
28. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
29. Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. . J. Org. Chem. 1993, 58, 4539; Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624; previous Ti-catalyzed oxidations of sulfides using other ligands: Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B.; J. Am. Chem. Soc. 1984, 106, 8188; Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109; Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325; see also Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2883, and lit. cited therein.
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35. 3).
36. -3. O1-O2 2.572(4) Å, O4-O5 2.554(5) Å. Atomic coordinates and e.s.d.'s have been deposited at the Cambridge Crystallographic Data Centre.
37. 8 affording 52% of S-5 having an ee-value of 86%.