The Unique Behavior of a Chiral Binaphthyl Oxazoline in the Presence of Cu(I) and Its Role as a Chiral Catalyst

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 412-413

  Meyers, A I ^a   Price, Alan ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000216282     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971761w     Document Type: Article

References (16)

1. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
2. Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869.
3. For recent reviews see: (a) Rossini, C.; Fannzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. (b) Narasaka, K Synthesis 1991, 1. Tomioka, K. Synthesis 1990, 541.
4. For recent reviews see: (a) Rossini, C.; Fannzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. (b) Narasaka, K Synthesis 1991, 1. Tomioka, K. Synthesis 1990, 541.
5. For recent reviews see: (a) Rossini, C.; Fannzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. (b) Narasaka, K Synthesis 1991, 1. Tomioka, K. Synthesis 1990, 541.
6. Fuji, K.; Sakurai, M.; Tohkai, N.; Kuroda, A.; Kawabata, T.; Fukazawa, Y.; Kinoshita, T.; Tada, T. J. Chem. Soc., Chem. Commun. 1996, 1609.
7. Harris, M. M.; Patel, P. K.; Korp, J. D.; Bernal, I. J. Chem. Soc., Perkin Trans. 2 1981, 12, 1621 and earlier references cited.
8. Fabbri, D.; Delogu, G.; DeLucchi, O. J. Org. Chem. 1995, 60, 6599.
9. Fuji, K.; Kawabata, T.; Kuroda, A.; Taga, T. J. Org. Chem. 1995, 60, 1914.
10. Artz, S. P.; deGrandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486.
11. (a) Ojima, I. Catalytic Asymmetric Synthesis; VCH: New York, 1993.
12. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. See also: Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603.
13. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. See also: Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603.
14. A recent report (Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745) described the use of chiral biphenyloxazolines as effective Cu-ligands for cyclopropanation.
15. It is important to recall, as mentioned earlier, that 4 cannot be transformed into 5 unless it is heated to 90-100°C in the presence of CuBr in DMF. Thus, at room temperature, only a "vague complex" or aggregate is formed between Cu(I) and 4.
16. Aggregations of Cu(I)·oxazoline complexes have been reported (Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430).