Asymmetric 1,4-Addition of Organocuprates to Chiral αβ-Unsaturated N-Acyl-4-phenyl-2-oxazolidinones: A New Approach to the Synthesis of Chiral β-Branched Carboxylic Acids

Journal of Organic Chemistry

Volumn 58, Issue 3, 1993, Pages 766-770

  Nicolás, Ernesto ^a,b   Russell, K C ^a   Hruby, Victor J ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001311213     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00055a039     Document Type: Note

References (23)

1. Hruby, V. J.; Pettitt, B. M. In Computer Drug Design; Perun, T. J., Propst, C., Eds.; Marcel Dekker: New York, 1989; p 405.
2. Kazmierski, W.; Hruby, V. J. Tetrahedron 1988, 44, 697.
3. Hruby, V. J.; Kazmierski, W.; Pelton, J. T.; Shook, J. E.; Knapp, R. J.; Burks, T. K.; Yamamura, H. I. In Peptide Chemistry 1987; Shiba, T., Sakakibara, S., Eds.; Prot. Res. Found.: Osaka, 1988, p 601.
4. Hruby, V. J.; Kao, L. F.; Hirning, L. D.; Burks, T. F. In Peptides—Structure and Function; Deber, C. M., Hruby, V. J.; Kopple, K. D., Eds.; Pierec Chemical Co.: Rockford, IL, 1985; p 487.
5. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
6. Dharanipragada, R.; Nicolas, E.; Toth, G.; Hruby, V. J. Tetrahedron Lett. 1989, 30, 6841.
7. Nicolas, E.; Dharanipragada, R.; Toth, G.; Hruby, V. J. Tetrahedron Lett. 1989, 30, 6845.
8. Evans, D. A.; Ellman, J. A.; Dorow, R. L. Tetrahedron Lett. 1987, 28 1123
9. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757.
10. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771 and referenced cited therein.
11. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
12. Melnyk, O.; Stephen, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841.
13. Wu, M.-J.; Wu, Ch.-Ch.; Lee, P.-Ch. Tetrahedron Lett. 1992, 33, 2547.
14. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3783.
15. Ito, Y.; Sasaki, A.; Tamoto, K.; Sunagawa, M.; Terashima, S. Tetrahedron 1991, 47, 2801.
16. Pridgen, L. N.; Prol, J.; Alexander, B.; Gillyard, L. J. Org. Chem. 1989, 54, 3231.
17. Giannis, A.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 218.
18. Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525.
19. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
20. Prelog, V.; Scherrer, H. Helv. Chim. Acta 1959, 42, 2227.
21. Oppolzer, W.; Mills, R. J.; Rachinger, W.; Stevenson, T. Helv. Chim. Acta 1986, 69, 1542.
22. Puscaru, E.; Zotta, V.; Serper, A.; Popescu, M.; Hociung, J.; Gasnet, A.; Spataru, R. Farmacia 1961, 9, 345.
23. Pearson, A. J.; Perrior, T. R. J. Chem. Soc., Perkin Trans. 1 1983, 625.