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Volumn 344, Issue 1, 2002, Pages 3-15

Linked-BINOL: An Approach towards Practical Asymmetric Multifunctional Catalysis

Author keywords

Asymmetric catalysis; Bimetallic complex; BINOL; Bridging ligands; Lanthanum; Multifunctional catalysis

Indexed keywords


EID: 0001304728     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200201)344:1<3::AID-ADSC3>3.0.CO;2-2     Document Type: Review
Times cited : (127)

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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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    • 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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    • 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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    • The recovered complex 20 contained -10-15% of 19
    • The recovered complex 20 contained -10-15% of 19.
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    • and references therein
    • 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]
    • 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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