Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 22, 1998, Pages 3657-3658

  Bull, Steven D ^a   Davies, Stephen G ^a   O'Shea, Michael D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748718541     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807618i     Document Type: Article

References (11)

1. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989;
2. R. O. Duthaler, Tetrahedron, 1994, 50, 1540.
3. S. D. Bull, S. G. Davies, S. W. Epstein and, J. V. A. Ouzman, Chem. Commun., 1998, 659.
4. S. D. Bull, S. G. Davies, S. W. Epstein and J. V. A. Ouzman, Tetrahedron: Asymmetry, 1998, 9, 2795.
5. Similar approaches have been adopted by Seebach et al. who employed a racemic methylene imidazolidinone auxiliary in a diastereoselective butylcuprate addition (D. Seebach, H. M. Bürger and C. P. Schickli, Liebigs. Ann. Chem., 1991, 669)
6. and by Hegedus et al. who used optically active carbamatoacrylates (P. A. Lander and L. S. Hegedus, J. Am. Chem. Soc., 1994, 116, 8126).
7. The stereochemistry of cis-(3S,6S)-benzylated DKP 7 was assigned by comparison with an authentic sample prepared de novo from (S)-phenylalanine and (S)-valine as described in reference 3.
8. C. Deng, U. Groth and U. Schöllkopf, Angew. Chem., Int. Ed. Engl., 1981, 21, 798;
9. U. Schöllkopf, Pure Appl. Chem., 1983, 55, 1799;
10. U. Schöllkopf, U. Busse, R. Lonsky and R. Hinrichs, Liebigs. Ann. Chem., 1986, 2150.
11. J. Pospicek and K. Blaha, Collect. Czech. Chem. Commun., 1987, 514.