Mechanistic investigation of the asymmetric addition of trimethylsilyl cyanide to aldehydes catalysed by dinuclear chiral (salen)titanium complexes

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2655-2661

  Belokon', Yuri N ^a   Green, Brendan ^b   Ikonnikov, Nicolai S ^a   Larichev, Vladimir S ^a   Lokshin, Boris V ^a   Moscalenko, Margarita A ^a   North, Michael ^c   Orizu, Charles ^b   Peregudov, Alexander S ^a   Timofeeva, Galina I ^a  

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

^b BANGOR UNIVERSITY   (United Kingdom)

^c KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Aldehydes; Asymmetric catalysis; Cyanohydrins; Titanium

Indexed keywords

ALDEHYDE DERIVATIVE; CYANIDE; TITANIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION;

EID: 0033868265     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2655::aid-ejoc2655>3.3.co;2-f     Document Type: Article

References (45)

1. Y. N. Belokon', S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Khrustalev, V. S. Larichev, M. A. Moscalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, L. V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968-3973.
2. Y. N. Belokon', B. Green, N. S. Ikonnikov, M. North, V. I. Tararov, Tetrahedron Lett. 1999, 40, 8147-8150.
3. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
4. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
5. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
6. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
7. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
8. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
9. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
10. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
11. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
12. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
13. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
14. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
15. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
16. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
17. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
18. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
19. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
20. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
21. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
22. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
23. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
24. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
25. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
26. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
27. For other work on the development of transition metal based catalysts for asymmetric cyanohydrin synthesis see: M. T. Reetz, F. Kunisch, P. Heitmann, Tetrahedron Lett. 1986, 27, 4721-4724; M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; H. Ohno, H. Nitta, K. Tanaka, A. Mori, S. Inoue, J. Org. Chem. 1992, 57, 6778-6783; A. Mori, H. Ohno, H. Nitta, K. Tanaka, S. Inoue, Synlett 1991, 563-564; B. Kaptein, V. Monaco, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 231-238; I. Iovel, Y. Popelis, M. Fleisher, E. Lukevics, Tetrahedron: Asymmetry 1997, 8, 1279-1285; S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 541-544; E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004; C. M. Garner, J. M. Fernandez, J. A. Gladysz, Tetrahedron Lett. 1989, 30, 3931-3934; M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946; A. Abiko, G.-q. Wang, J. Org. Chem. 1996, 61, 2264-2265; W. B. Yang, J. M. Fang, J. Org. Chem. 1998, 63, 1356-1359; C. Qian, C. Zhu, T. Huang, J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132; A. Abiko, G.-q. Wang, Tetrahedron 1998, 54, 11405-11420; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Chem. Commun. 1990, 1364-1365; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, 1 1992, 3135-3140; C. Bolm, P. Müller, Tetrahedron Lett. 1995, 36, 1625-1628; C. Bolm, P. Müller, K. Harms, Acta Chem. Scand. 1996, 50, 305-315; M. Hayashi, Y. Miyamoto, T Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398; M. Hayashi, Y. Miyamoto, T. Inoue, M. Oguni, J. Chem. Soc., Chem. Commun. 1991, 1752-1753; Y. Jiang, X. Zhou, W. Hu, L. Wu, A. Mi, Tetrahedron: Asymmetry 1995, 6, 405-408; Y. Jiang, X. Zhou, W. Hu, Z. Li, A. Mi, Tetrahedron: Asymmetry 1995, 6, 2915-2916; A. Mori, H. Nitta, M. Kudo, S. Inoue, Tetrahedron Lett. 1991, 32, 4333-4336; Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641 -2642.
28. C. E. Housmekerides, D. L. Ramage, C. M. Kretz, J. T. Shontz, R. S. Pilato, G. L. Geoffroy, A. L. Rheingold, B. S Haggerty, Inorg. Chem.. 1992, 31, 4453-4468.
29. For examples of asymmetric cyanohydrin forming reactions which have been proposed to involve a chiral cyanide source see: K. Narasaka, T. Yamada, H. Minamikawa. Chem. Lett. 1987, 2073-2076; H. Minamikawa, S. Hayakawa, T. Yamada. N. Iwasawa, K. Narasaka, Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383.
30. For examples of asymmetric cyanohydrin forming reactions which have been proposed to involve a chiral cyanide source see: K. Narasaka, T. Yamada, H. Minamikawa. Chem. Lett. 1987, 2073-2076; H. Minamikawa, S. Hayakawa, T. Yamada. N. Iwasawa, K. Narasaka, Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383.
31. For examples of asymmetric cyanohydrin forming reactions which have been proposed to involve a chiral Lewis acid see: H. Nitta, D. Yu, M. Kudo, A. Mori, S. Inoue, J. Am. Chem. Soc. 1992, 114, 7969-7975; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans. 2 1992, 3135-3140; M. Mori, H. Imma, T. Nakai, Tetrahedron Lett. 1997, 38, 6229-6232.
32. For examples of asymmetric cyanohydrin forming reactions which have been proposed to involve a chiral Lewis acid see: H. Nitta, D. Yu, M. Kudo, A. Mori, S. Inoue, J. Am. Chem. Soc. 1992, 114, 7969-7975; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans. 2 1992, 3135-3140; M. Mori, H. Imma, T. Nakai, Tetrahedron Lett. 1997, 38, 6229-6232.
33. For examples of asymmetric cyanohydrin forming reactions which have been proposed to involve a chiral Lewis acid see: H. Nitta, D. Yu, M. Kudo, A. Mori, S. Inoue, J. Am. Chem. Soc. 1992, 114, 7969-7975; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans. 2 1992, 3135-3140; M. Mori, H. Imma, T. Nakai, Tetrahedron Lett. 1997, 38, 6229-6232.
34. There is a single example of a seven co-ordinate titanium salen complex in the literature. However, in this case the aromatic rings were unsubstituted, two relatively small chlorine atoms were co-ordinated to the titanium, and the seventh ligand was a complexed thf solvent molecule: S. J. Coles, M. B. Hursthouse, D. G. Kelly, A. J. Toner, N. M. Walker, J. Chem. Soc., Dalton Trans. 1998, 3489-3494.
35. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
36. J. A. Marshall, Chem. Rev. 1996, 96, 31-47; C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
37. J. A. Marshall, Chem. Rev. 1996, 96, 31-47; C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
38. C. Gennari, in: Comprehensive Organic Synthesis: Additions to C-X π Bonds Part 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon Press: New York, 1991, Chapter 2.4.
39. A. Pasini, M. Gullotti, R. Ugo, J. Chem. Soc., Dalton Trans. 1977, 346-356; M. Gullotti, A. Pasini, G. M. Zanderighi, G. Ciani, A. Sironi, J. Chem. Soc., Dalton Trans. 1981, 902-908.
40. A. Pasini, M. Gullotti, R. Ugo, J. Chem. Soc., Dalton Trans. 1977, 346-356; M. Gullotti, A. Pasini, G. M. Zanderighi, G. Ciani, A. Sironi, J. Chem. Soc., Dalton Trans. 1981, 902-908.
41. W. R. Entley, C. R. Treadway, S. R. Wilson, G. S. Girolami, J. Am. Chem. Soc. 1997, 119, 6251-6258.
42. K. Nakamoto, Infrared and Roman Spectra of Inorganic and Coordination Compounds, 4-th Ed. Wiley: New York, 1986, 272-280.
43. 3 group see: F. J. Feher, S. L. Gonzales, J. W. Ziller, Inorg. Chem. 1988, 27, 3440-3442.
44. For mononuclear complexes, a planar coordination of salen ligands is known to be preferred to a nonplanar coordination: R. Rajan, V. Subramanian, B. Umni-Nair, T. Ramasami, Bull. Chem. Soc. Jpn. 1998, 71, 1293-1298.
45. Y. N. Belokon', N. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V. Tararov, L. Yashkina, Tetrahedron: Asymmetry 1996, 7, 851-855.