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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For selected examples of recent bifunctional asymmetric catalysts, see: M. Yamanaka, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466; J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687; B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656; G. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389; A. J. Blake, A. Cunningham, A. Ford, S. J. Teat, S. Woodward, Chem. Eur. J. 2000, 6, 3586; B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003; E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641, and references therein. For early works on bifunctional asymmetric catalysts, see ref. [19]. See, also Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405; A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649.
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For related works by other groups concerning linked-BINOLs and polymer-BINOLs, see; H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500, and references therein; T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261; H. Ishitani, T. Kitazawa, S. Kobayashi, Tetrahedron Lett. 1999, 40, 2161; A. Cunningham, M. R. Dennis, S. Woodward, J. Chem. Soc. Perkin Trans. 1 2000, 4422, and references therein; H.-F. Chow, M.-K. Ng, Tetrahedron: Asymmetry 1996, 7, 2251; Y. Meng, W. T. Slaven IV, D. Wang, T.-J. Liu, H.-F. Chow, C.-J. Li, Tetrahedron: Asymmetry 1998, 9, 3693.
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For related works by other groups concerning linked-BINOLs and polymer-BINOLs, see; H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500, and references therein; T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261; H. Ishitani, T. Kitazawa, S. Kobayashi, Tetrahedron Lett. 1999, 40, 2161; A. Cunningham, M. R. Dennis, S. Woodward, J. Chem. Soc. Perkin Trans. 1 2000, 4422, and references therein; H.-F. Chow, M.-K. Ng, Tetrahedron: Asymmetry 1996, 7, 2251; Y. Meng, W. T. Slaven IV, D. Wang, T.-J. Liu, H.-F. Chow, C.-J. Li, Tetrahedron: Asymmetry 1998, 9, 3693.
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(R)- and (S)-BINOL were purchased from Kankyo Kagaku Center Co., LTD., 5-1, Ookawa, Kanazawa-ku, Yokohama-city, Kanagawa, 236-8605, Japan [fax: +(81)-45-701-6145. (R)-BINOL: 500 g, 60,000 yen (ca. 500 US$), (S)-BINOL: 500 g, 42,000 yen (ca. 350 US$)]
-
(R)- and (S)-BINOL were purchased from Kankyo Kagaku Center Co., LTD., 5-1, Ookawa, Kanazawa-ku, Yokohama-city, Kanagawa, 236-8605, Japan [fax: +(81)-45-701-6145). (R)-BINOL: 500 g, 60,000 yen (ca. 500 US$), (S)-BINOL: 500 g, 42,000 yen (ca. 350 US$)].
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For representative examples of other recent catalytic asymmetric Michael reaction with carbon nucleophiles, see: B. L. Feringa, Acc. Chem. Res. 2000, 33, 346; T. Hayashi, T. Senda, M. Ogasawara, J. Am. Chem. Soc. 2000, 122, 10716; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480; J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenberger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215, and references therein. For other examples, see ref.[37].
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For representative examples of other recent catalytic asymmetric Michael reaction with carbon nucleophiles, see: B. L. Feringa, Acc. Chem. Res. 2000, 33, 346; T. Hayashi, T. Senda, M. Ogasawara, J. Am. Chem. Soc. 2000, 122, 10716; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480; J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenberger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215, and references therein. For other examples, see ref.[37].
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and references therein. For other examples, see ref.[37]
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For representative examples of other recent catalytic asymmetric Michael reaction with carbon nucleophiles, see: B. L. Feringa, Acc. Chem. Res. 2000, 33, 346; T. Hayashi, T. Senda, M. Ogasawara, J. Am. Chem. Soc. 2000, 122, 10716; E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347; D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480; J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenberger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215, and references therein. For other examples, see ref.[37].
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104
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0346368213
-
-
note
-
In terms of reactivity, catalyst amount, and cost efficiency, ALB is the most effective for the present Michael reaction in large scale synthesis. Enantiomerically pure Michael adduct 29 was easily obtained in a 100-g scale reaction by recrystallization, see, ref.[36].
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105
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0001392528
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Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507.
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106
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0345737040
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3 was purchased from Kojundo Chemical Laboratory Co., Ltd., 5-1-28, Chiyoda, Sakado-shi, Saitama 350-0214, Japan [fax: + (81)-492-84-1351]
-
3 was purchased from Kojundo Chemical Laboratory Co., Ltd., 5-1-28, Chiyoda, Sakado-shi, Saitama 350-0214, Japan [fax: + (81)-492-84-1351].
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-
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107
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0346368218
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The recovered complex 20 contained -10-15% of 19
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The recovered complex 20 contained -10-15% of 19.
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For selected examples of recent dinuclear Zn catalysts, see refs.[20f,49] and references cited therein. See also, S. Hikichi, M. Tanaka, Y. Moro-oka, N. Kitajima, J. Chem. Soc. Chem. Commun. 1992, 814; W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; M. Yashiro, A. Ishikubo, M. Komiyama, J. Chem. Soc. Chem. Commun. 1995, 1793; T. Koike, M. Inoue, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1996, 118, 3091; P. Molenveld, S. Kapsabeils, J. F. J. Engbersen, D. N. Reinhoudt, J. Am. Chem. Soc. 1997, 119, 2948; C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, C. Giorgi. P. Paoletti, B. Valtancoli, D. Zanchi, Inorg. Chem. 1997, 36, 2784; N. V. Kaminskaia, B. Spingler, S. J. Lippard, J. Am. Chem. Soc. 2000, 122, 6411; P. Rossi, F. Felluga, P. Tecilla, F. Formaggio, M. Crisma, C. Toniolo, P. Scrimin, J. Am. Chem. Soc. 1999, 121, 6948; H.-S. Kim, J.-J. Kim, B.-G. Lee, O.-S. Jung, H.-G. Jang, S.-O. Kang, Angew. Chem. Int. Ed. 2000, 39, 4096; K. Abe, J. Izumi, M. Ohba, T. Yokoyama, H. Okawa, Bull. Chem. Soc. Jpn. 2001, 74, 85, and references therein.
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For selected examples of recent dinuclear Zn catalysts, see refs.[20f,49] and references cited therein. See also, S. Hikichi, M. Tanaka, Y. Moro-oka, N. Kitajima, J. Chem. Soc. Chem. Commun. 1992, 814; W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; M. Yashiro, A. Ishikubo, M. Komiyama, J. Chem. Soc. Chem. Commun. 1995, 1793; T. Koike, M. Inoue, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1996, 118, 3091; P. Molenveld, S. Kapsabeils, J. F. J. Engbersen, D. N. Reinhoudt, J. Am. Chem. Soc. 1997, 119, 2948; C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, C. Giorgi. P. Paoletti, B. Valtancoli, D. Zanchi, Inorg. Chem. 1997, 36, 2784; N. V. Kaminskaia, B. Spingler, S. J. Lippard, J. Am. Chem. Soc. 2000, 122, 6411; P. Rossi, F. Felluga, P. Tecilla, F. Formaggio, M. Crisma, C. Toniolo, P. Scrimin, J. Am. Chem. Soc. 1999, 121, 6948; H.-S. Kim, J.-J. Kim, B.-G. Lee, O.-S. Jung, H.-G. Jang, S.-O. Kang, Angew. Chem. Int. Ed. 2000, 39, 4096; K. Abe, J. Izumi, M. Ohba, T. Yokoyama, H. Okawa, Bull. Chem. Soc. Jpn. 2001, 74, 85, and references therein.
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For selected examples of recent dinuclear Zn catalysts, see refs.[20f,49] and references cited therein. See also, S. Hikichi, M. Tanaka, Y. Moro-oka, N. Kitajima, J. Chem. Soc. Chem. Commun. 1992, 814; W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; M. Yashiro, A. Ishikubo, M. Komiyama, J. Chem. Soc. Chem. Commun. 1995, 1793; T. Koike, M. Inoue, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1996, 118, 3091; P. Molenveld, S. Kapsabeils, J. F. J. Engbersen, D. N. Reinhoudt, J. Am. Chem. Soc. 1997, 119, 2948; C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, C. Giorgi. P. Paoletti, B. Valtancoli, D. Zanchi, Inorg. Chem. 1997, 36, 2784; N. V. Kaminskaia, B. Spingler, S. J. Lippard, J. Am. Chem. Soc. 2000, 122, 6411; P. Rossi, F. Felluga, P. Tecilla, F. Formaggio, M. Crisma, C. Toniolo, P. Scrimin, J. Am. Chem. Soc. 1999, 121, 6948; H.-S. Kim, J.-J. Kim, B.-G. Lee, O.-S. Jung, H.-G. Jang, S.-O. Kang, Angew. Chem. Int. Ed. 2000, 39, 4096; K. Abe, J. Izumi, M. Ohba, T. Yokoyama, H. Okawa, Bull. Chem. Soc. Jpn. 2001, 74, 85, and references therein.
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Both (R,R)- and (5,S)-La-linked-BINOL complexes are commercially available from Strem Chemicals, Inc. [Catalog No. 57-0200 for (R,R)-catalyst and 57-0201 for (S,S)-catalyst]
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Both (R,R)- and (5,S)-La-linked-BINOL complexes are commercially available from Strem Chemicals, Inc. [Catalog No. 57-0200 for (R,R)-catalyst and 57-0201 for (S,S)-catalyst].
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