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Volumn 44, Issue 14, 2003, Pages 2947-2951

Enantiomerically pure phenanthroline or bipyridine containing macrocycles: A new class of ligands for asymmetric catalysis

Author keywords

Asymmetric catalysis; Chiral phenanthrolines; Copper(I) complexes; Cyclopropanation; Enantiomerically pure macrocycles

Indexed keywords

ALKENE DERIVATIVE; BIPYRIDINE DERIVATIVE; CIS ACTING ELEMENT; COPPER COMPLEX; LIGAND; MACROCYCLIC COMPOUND; PHENANTHROLINE DERIVATIVE; TRANS ACTING FACTOR;

EID: 0037474678     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00425-8     Document Type: Article
Times cited : (44)

References (44)
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    • For other relevant examples of chiral macrocyles, see also: (a) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165-167; (b) Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron Lett. 2000, 41, 3137-3140; (c) Habata, Y.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. J. Am. Chem. Soc. 1997, 119, 7145-7146.
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    • For other relevant examples of chiral macrocyles, see also: (a) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165-167; (b) Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron Lett. 2000, 41, 3137-3140; (c) Habata, Y.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. J. Am. Chem. Soc. 1997, 119, 7145-7146.
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    • For other relevant examples of chiral macrocyles, see also: (a) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165-167; (b) Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron Lett. 2000, 41, 3137-3140; (c) Habata, Y.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. J. Am. Chem. Soc. 1997, 119, 7145-7146.
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    • note
    • The reaction of diacid 3 with 6 afforded only mixtures of products.
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    • note
    • The reaction of diol 4 with phenanthroline 7 afforded only mixtures of products.
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    • For the preparation of 2,9-bis-(4-hydroxypheny)-1,10-phenanthroline, see: and references cited therein
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    • 1H NMR analysis on the isolated diastereoisomers.
    • 1H NMR analysis on the isolated diastereoisomers.
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    • All the new products were fully characterized and show spectral data in agreement with the proposed structure (see Supporting Information).
    • All the new products were fully characterized and show spectral data in agreement with the proposed structure (see Supporting Information).
  • 40
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    • The reaction did not proceed at temperature lower than -20°C.
    • The reaction did not proceed at temperature lower than -20°C.
  • 41
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    • and references cited therein
    • Only a few examples of high cis-stereoselectivity for the cyclopropanation of styrene with ethyldiazoacetate are known, see: (a) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79-88 and references cited therein; (b) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102-2108; (c) Zheng, Z.; Yao, X.; Li, C.; Chen, H.; Hu, X. Tetrahedron Lett. 2001, 42, 2847-2849; (d) Doyle, P. M.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867-868 and references cited therein.
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    • Only a few examples of high cis-stereoselectivity for the cyclopropanation of styrene with ethyldiazoacetate are known, see: (a) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79-88 and references cited therein; (b) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102-2108; (c) Zheng, Z.; Yao, X.; Li, C.; Chen, H.; Hu, X. Tetrahedron Lett. 2001, 42, 2847-2849; (d) Doyle, P. M.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867-868 and references cited therein.
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    • Only a few examples of high cis-stereoselectivity for the cyclopropanation of styrene with ethyldiazoacetate are known, see: (a) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79-88 and references cited therein; (b) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102-2108; (c) Zheng, Z.; Yao, X.; Li, C.; Chen, H.; Hu, X. Tetrahedron Lett. 2001, 42, 2847-2849; (d) Doyle, P. M.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867-868 and references cited therein.
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    • and references cited therein
    • Only a few examples of high cis-stereoselectivity for the cyclopropanation of styrene with ethyldiazoacetate are known, see: (a) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79-88 and references cited therein; (b) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102-2108; (c) Zheng, Z.; Yao, X.; Li, C.; Chen, H.; Hu, X. Tetrahedron Lett. 2001, 42, 2847-2849; (d) Doyle, P. M.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867-868 and references cited therein.
    • (2000) Chem. Commun. , pp. 867-868
    • Doyle, P.M.1    Davies, S.B.2    Hu, W.3


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