1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 163-166

  Hanessian, Stephen ^a   Schaum, Robert ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ALKYLATION; ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031032162     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02263-0     Document Type: Article

References (29)

1. For recent reviews on amino acids, see a) Duthaler, R. O. Tetrahedron 1994, 50, 1539;
2. b) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360;
3. c) Williams, R. H. in "The Synthesis of Optically Active α-Amino Acids", New York, Pergamon, 1989;
4. d) Coppola, G. M. and Shuster, H. F. in "Asynunetric Synthesis: Construction of Chiral Molecules Using Amino Acids" New York, Toronto, Wiley, 1987.
5. a) Seebach, D.; Aebi, J.; Wasmuth, D. Org. Synth. 1984, 63, 109;
6. b) Seebach, D.; Wasmuth, D. Angew. Chem. Int. Ed. Engl. 1981, 20, 971;
7. c) Seebach, D.; Weller, T.; Züger, M. Helv. Chim. Acta. 1980, 63, 2005;
8. d) Seebach, D.; Wasmuth, D. Helv. Chim. Acta. 1980, 63, 197;
9. e) Fräter, G. Helv. Chim. Acta 1979, 62, 2829.
10. a) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1994, 59, 649;
11. b) Seebach, D.; Estermann, H. Helv. Chim. Acta. 1988, 71, 1824.
12. a) Narasaka, K.; Yutaka, U. Bull. Chem. Soc. Jpn. 1988, 61, 571;
13. b) Narasaka, K.; Ukaji, Y. Chem. Lett. 1986, 81.
14. Wittenberger, S. J.; Boyd, S. A.; Baker, W. R. Synlett 1993, 795.
15. a) Parr, I. B.; Boehlein, S. K.; Dribben, A. B.; Schuster, S. M.; Richards, N. G. J. J. Med. Chem. 1996, 39, 2367;
16. b) Dunn, P. J; Haner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017;
17. c) Baldwin, J. E.; Moloney, M. G.; North, M. Tetrahedron 1989, 45, 6309;
18. d) Baldwin, J. E.; Moloney, M. G.; North, M. J. Chem. Soc. Perkin Trans.l 1989, 833.
19. a) Gu Z-Q.; Hesson D. P. Tetrahedron Lett. 1995, 6, 2101;
20. b) Johnstone, A. N. C.; Lopatriello, S.; North, M. Tetrahedron Lett. 1994, 35, 6335;
21. c) Baldwin, J. E.; North, M.; Flinn, A.; Moloney, M. G. J. Chem. Soc., Chem. Commun. 1988, 828.
22. a) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401;
23. b) Vanasse, B., Ph.D. thesis, University of Montréal, 1991.
24. For a recent example of 1,3-asymmetric induction in the α-hydroxylation of a ketone enolate, see Alexander, C. W.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 1961.
25. Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996,118, 2507.
26. Posner, G. H.; Lentz, C. M. J. Am. Chem. Soc. 1979, 101, 934.
27. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
28. a) Feigel, M.; Martinek, G.; Sauer, W. H. B. Chem. Eur. J. 1996, 2, 9;
29. b) Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624.