Homochiral 2,2′-bis(oxazolyl)-1,1′-binaphthyls as ligands for copper(I)-catalyzed asymmetric cyclopropanation

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1603-1606

  Uozumi, Yasuhiro ^a   Kyota, Hirokazu ^a   Kishi, Eiji ^a   Kitayama, Kenji ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; OXAZOLINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHIRALITY; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; LIGAND BINDING; PRIORITY JOURNAL;

EID: 0029882378     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00193-0     Document Type: Article

References (26)

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3. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
4. (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
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6. (c) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta. 1991, 74, 232.
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12. (c) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
13. During the preparation of this manuscript, a study was reported describing asymmetric intramolecular cyclopropanation with a 2,2′-bis(oxazolyl)-6,6′-dimethyl-1,1′-biphenyl: Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
14. Compounds (S,S)-1a-c and (S,R)-1a-c have appeared as intermediates for synthesis of optically active binaphthyldicarboxylic acid, which were prepared by enantioselective Ullmann coupling of corresponding 1-bromo-2-(oxazolyl)naphthalenes: Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
15. 2.
16. Vorbruggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471.
17. 1H NMR data with those reported by A. I. Meyers: Meyers, A. I. private communication. Also see ref 6.
18. Because of difficulty in separation of the diastereomers, isomerically pure (S,S)-1d was prepared from enantiomerically pure (S)-2 according to the same synthetic sequences shown in Scheme 1.
19. 20 -91 (c 0.78, chloroform).
20. For a recent review on catalytic asymmetric cyclopropanations: Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 63.
21. For recent examples: (a) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 430.
22. (b) Piqué, C.; Fähndrich, B.: Pfaltz, A. Synlett 1995, 491.
23. Tokunoh, R.; Tomiyama, H.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449. See also ref 3a-d.
24. 1H NMR and GC analysis to determine the diastereomeric ratio and the enantiomeric excess (see text).
25. D+296 (c 0.88, chloroform), respectively. See ref 3d.
26. 4.