Enantioselective trimethylsilylcyanation of aromatic aldehydes catalyzed by titanium alkoxide-chiral o-hydroxyarylphosphine oxides complexes

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1979-1984

  Brunel, Jean Michel ^a   Legrand, Olivier ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PHOSPHINE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033591128     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00179-2     Document Type: Article

References (35)

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10. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
11. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
12. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
13. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
14. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
15. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
16. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
17. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
18. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
19. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
20. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
21. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
22. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
23. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
24. For significant publications dealing with asymmetric trimethylsilylcyanation reactions, see: (a) Hwang, C. D.; Hwang, D. R.; Uang, B. J. J. Org. Chem. 1998, 63, 6762. (b) Tararov, V.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. Chem. Commun. 1998, 387. (c) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1998, 53, 14327. (d) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229. (e) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293. (f) Choi, M. C. K.; Chan, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669. (g) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rosenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245. (h) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851. (i) Bolm, C.; Muller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305. (j) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131. (k) Yang, W. B.; Fang, J. M. J. Org. Chem. 1998, 63, 1356. (l) Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279. (m) Wada, M.; Takahashi, T.; Domae, T.; Fukama, T.; Miyoshi, N.; Smith, K. Tetrahedron: Asymmetry 1997, 8, 3939. (n) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385. (o) Abiko, A.; Wang, G. Q. J. Org. Chem. 1996, 61, 2264.
25. (a) Legrand, O.; Brunel, J. M.; Constantieux, T.; Buono, G. Chem. Eur. J. 1998, 4, 1061.
26. (b) Legrand, O.; Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 1999, in press.
27. These compounds may be reviewed as analogues of 1,3-diketone type ligand of various transition metals. They may form complexes with metal ions and have been used in the preparation of ligands capable of extracting ammonium compounds from aqueous to organic phases. Alberts, A. H.; Timmer, K.; Noltes, J. G.; Spek, A. L. J. Am. Chem. Soc. 1979, 101, 3375.
28. (a) Brunel, J. M.; Constantieux, T.; Legrand, O.; Buono, G. Tetrahedron Lett. 1998, 39, 2961.
29. (b) Legrand, O.; Brunel, J. M.; Buono, G. Tetrahedron Lett. 1998, 39, 9419.
30. 4 and anti-1a, in a 1:4 molar ratio led to the formation of mandelonitrile in 91% yield and 36% ee.
31. Similar results have been previously reported by Oguni et al. using a modified Sharpless catalyst. In this case, it has been clearly demonstrated that the resulting active species are different depending on the method used for the preparation of the titanium catalyst, (a) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1992, 3135. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364.
32. Similar results have been previously reported by Oguni et al. using a modified Sharpless catalyst. In this case, it has been clearly demonstrated that the resulting active species are different depending on the method used for the preparation of the titanium catalyst, (a) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1992, 3135. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364.
33. About nonlinear effects in asymmetric catalysis, see: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922. (b) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353. (c) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
34. About nonlinear effects in asymmetric catalysis, see: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922. (b) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353. (c) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
35. About nonlinear effects in asymmetric catalysis, see: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922. (b) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353. (c) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.