(α-Aminoalkyl)cuprates Prepared from Soluble Copper(I) Salts: Conjugate Additions to α,βUnsaturated Carboxylic Acid Derivatives

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3798-3799

  Dieter, R Karl ^a   Velu, Sadanandan E ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001504725     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970443u     Document Type: Article

References (23)

1. (a) Dieter, R. K.; Alexander, C. W. Synlett 1993, 407.
2. (b) Dieter, R. K.; Alexander, C. W. Tetrahedron Lett. 1992, 33, 5693.
3. Lipshutz, B. H. Tetrahedron Lett. 1983, 24, 127.
4. Behforousz, M.; Curran, T. T.; Bolan, J. Ibid. 1986, 27, 3107.
5. Sakata, H.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 5719.
6. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047.
7. (a) Bergdahl, M.; Lindstedt, E.-L.; Nilsson, M. Tetrahedron 1988, 44, 2055.
8. (b) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119.
9. Bertz, S. H.; Gibson, C. P.; Dabbagh, G. Tetrahedron Lett. 1987 28, 4251.
10. (a) Bertz, S. H.; Miao, G.; Eriksson, M. J. Chem. Soc., Chem. Commun. 1996, 815.
11. (b) Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312.
12. (c) Barnhart, T. M.; Huang, H.; Penner-Hahn, J. E. J. Org. Chem. 1995, 60, 4310.
13. (d) Lipshutz, B. H.; James, B. Ibid. 1994, 59, 7585.
14. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
15. Backvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126.
16. (b) Schlosser, M.; Bossert, H. Tetrahedron 1991, 47, 6287.
17. Alexander, C. W. Ph.D Dissertation, Clemson University, 1993.
18. AM1 calculations obtained from the MacSpartan program. (Wavefunction, Inc., 18401 Von Karman Ave, #370, Irvine, CA 92715) gave the following relative ordering of LUMO energies: thiol esters < esters < imides. The calculated magnitude of the LUMO energies displayed no clear correlation with the observed chemical yields.
19. (a) Anderson, R. J.; Henrick, C. A.; Rosenblum, L. D. J. Am. Chem. Soc. 1974, 96, 3654.
20. (b) Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.; Nambiar, K. P.; Falck, J. R. Ibid. 1979, 101, 7131.
21. (c) Collum, D. B.; McDonald, J. H.; Still, W. C. Ibid. 1980, 102, 2120.
22. Krauss, S. R.; Smith, S. G. J. Am. Chem. Soc. 1981, 103, 141.
23. Hallnemo, G.; Ullenius, C. Tetrahedron Lett. 1986, 27, 395.