The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex

Tetrahedron Letters

Volumn 40, Issue 46, 1999, Pages 8147-8150

  Belokon, Yuri N ^b   Green, Brendan ^a   Ikonnikov, Nicolai S ^b   North, Michael ^a,c   Tararov, Vitali I ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Asymmetric synthesis; Catalysis; Cyanohydrins; Ketones; Salen; Titanium

Indexed keywords

CYANIC ACID DERIVATIVE; ETHER DERIVATIVE; KETONE DERIVATIVE; METAL COMPLEX; TITANIUM DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; ENANTIOMER; SYNTHESIS;

EID: 0033550302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01677-9     Document Type: Article

References (20)

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2. Griengl, H.; Hickel, A.; Johnson, D. V.; Kratky, C.; Schmidt, M.; Schwab, H. Chem. Commun. 1997, 1933, and referencescited therein. Kruse, C. G. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; chapter 14.
3. For reviews, see: North, M. Synlett 1993, 807. Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555. North, M.Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Pergamon Press: Oxford, 1995: Vol. 3, chapter 18.
4. For reviews, see: North, M. Synlett 1993, 807. Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555. North, M.Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Pergamon Press: Oxford, 1995: Vol. 3, chapter 18.
5. For reviews, see: North, M. Synlett 1993, 807. Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555. North, M. Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Pergamon Press: Oxford, 1995: Vol. 3, chapter 18.
6. Effenberger, F.; Horsch, B.; Weingart, F.; Ziegler, T.; Kuhner, S. Tetrahedron Lett. 1991, 32, 2605. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945. Foerster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551. Griengl, H.; Klempier, N.; Pochlaur, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477.
7. Effenberger, F.; Horsch, B.; Weingart, F.; Ziegler, T.; Kuhner, S. Tetrahedron Lett. 1991, 32, 2605. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945. Foerster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551. Griengl, H.; Klempier, N.; Pochlaur, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477.
8. Effenberger, F.; Horsch, B.; Weingart, F.; Ziegler, T.; Kuhner, S. Tetrahedron Lett. 1991, 32, 2605. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945. Foerster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551. Griengl, H.; Klempier, N.; Pochlaur, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477.
9. Effenberger, F.; Horsch, B.; Weingart, F.; Ziegler, T.; Kuhner, S. Tetrahedron Lett. 1991, 32, 2605. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945. Foerster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551. Griengl, H.; Klempier, N.; Pochlaur, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477.
10. Effenberger, F.; Horsch, B.; Weingart, F.; Ziegler, T.; Kuhner, S. Tetrahedron Lett. 1991, 32, 2605. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945. Foerster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551. Griengl, H.; Klempier, N.; Pochlaur, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477.
11. Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669.
12. Belokon', Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996. 7, 851. Belokon', Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M.J. Chem. Soc., Perkin Trans. 1 1997, 1293. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K.M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387. Belokon', Y. N.; Caveda-Cepas, S.; Green, B.;Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
13. Belokon', Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry1996. 7, 851. Belokon', Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K.M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387. Belokon', Y. N.; Caveda-Cepas, S.; Green, B.;Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
14. Belokon', Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry1996. 7, 851. Belokon', Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M.J. Chem. Soc., Perkin Trans. 1 1997, 1293. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387. Belokon', Y. N.; Caveda-Cepas, S.; Green, B.;Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
15. Belokon', Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry1996. 7, 851. Belokon', Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M.J. Chem. Soc., Perkin Trans. 1 1997, 1293. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K.M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387. Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
16. The use of similar titanium salen complexes to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes has also been reported: Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337. Jiang, Y.; Gong, L.;Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327. Belokon', Y. N.; Yashkina, L. V.; Moscalenko, M. A.; Chesnokov, A. A.; Kublitsky, V. S.; Ikonnikov, N. S.; Orlova, S. A.; Tararov, V. I.; North, M. Russian Chem. Bull.1997, 46, 1936. Belokon', Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rozenberg, V.Tetrahedron: Asymmetry 1997, 8, 3245.
17. The use of similar titanium salen complexes to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes hasalso been reported: Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337. Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327. Belokon', Y. N.; Yashkina, L. V.; Moscalenko, M. A.; Chesnokov, A. A.; Kublitsky, V. S.; Ikonnikov, N. S.; Orlova, S. A.; Tararov, V. I.; North, M. Russian Chem. Bull.1997, 46, 1936. Belokon', Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rozenberg, V.Tetrahedron: Asymmetry 1997, 8, 3245.
18. The use of similar titanium salen complexes to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes hasalso been reported: Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337. Jiang, Y.; Gong, L.;Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327. Belokon', Y. N.; Yashkina, L. V.; Moscalenko, M. A.; Chesnokov, A. A.; Kublitsky, V. S.; Ikonnikov, N. S.; Orlova, S. A.; Tararov, V. I.; North, M. Russian Chem. Bull. 1997, 46, 1936. Belokon', Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rozenberg, V.Tetrahedron: Asymmetry 1997, 8, 3245.
19. The use of similar titanium salen complexes to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes hasalso been reported: Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337. Jiang, Y.; Gong, L.;Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327. Belokon', Y. N.; Yashkina, L. V.; Moscalenko, M. A.; Chesnokov, A. A.; Kublitsky, V. S.; Ikonnikov, N. S.; Orlova, S. A.; Tararov, V. I.; North, M. Russian Chem. Bull.1997, 46, 1936. Belokon', Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rozenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245.
20. Recently Jacobsen reported the use of chiral aluminium salen complexes to induce the asymmetric addition of hydrogen cyanide to imines: Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.