Anti-selective aldol reactions of amino acid ester enolates. Application to the synthesis of α-alkylated β-hydroxy amino acids

Liebigs Annales

Volumn , Issue 7, 1996, Pages 1143-1150

  Grandel, Roland ^a   Kazmaier, Uli ^a   Nuber, Bernhard ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Aldol reactions; Amino acids; Chelated enolates; Hydroxy amino acids

Indexed keywords

EID: 33749124116     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960713     Document Type: Article

References (45)

1. H. Heimgartner, Angew. Chem. 1991, 103, 271-297;
2. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264.
3. R. R. Rando, Acc. Chem. Res. 1975, 8, 281-288;
4. J. J. Walsh, D. E. Metzler, D. Powell, R. A. Jacobsen, J. Am. Chem. Soc. 1980, 102, 7136-7138;
5. R. H. Abeles, Pure Appl. Chem. 1981, 53, 149-160;
6. C. Walsh, Tetrahedron 1982, 38, 871-909;
7. K. Ramalingam, R. W. Woodward, Tetrahedron Lett. 1985, 26, 1135-1136;
8. S. J. B. Tendler, M. D. Threadgill, M. J. Tisdale, J. Chem. Soc., Perkin Trans. 1, 1987, 2617-2623.
9. C. Tomiolo, M. Crisma, S. Pegoraro, E. L. Becker, S. Polinelli, W. H. J. Boesten, H. E. Schoemaker, E. M. Meijer, J. Kamphuis, R. Freer, Peptide Res. 1991, 4, 66.
10. P. K. C. Paul, M. Sukumar, R. Bardi, A. M. Piazzesi, G. Valle, C. Toniolo, P. Balaram, J. Am. Chem. Soc. 1986, 108, 6363-6370, and refs. therein.
11. W. S. Horn, J. L. Smith, G. F. Bills, S. L. Raghoobar, G. L. Helms, M. B. Kurtz, J. A. Marrinan, B. R. Frommer, R. A. Thornton, S. M. Mandala, J. Antibiot. 1992, 45, 1692-1696;
12. A. V. R. Rao, M. K. Gurjar, T. R. Devi, K. R. Kumar, Tetrahedron Lett. 1993, 34, 1653-1656.
13. T. Sunazuka, T. Nagamitsu, K. Matsuzaki, H. Tanaka, S. Omura, J. Am. Chem. Soc. 1993, 115, 5302;
14. E. J. Corey, S. Choi, Tetrahedron Lett. 1993, 34, 6969-6972.
15. For general reviews, see: R. M. Williams, Synthesis of Optically Active α-Amino Acids; Pergamon Press, Oxford, 1989;
16. R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650.
17. For some representative examples, see: [8a] U. Schöllkopf, U. Groth, W. Hartwig, Liebigs Ann. Chem. 1981, 2407-2418.
18. [8b] Y. N. Belokon, A. G. Bulychev, S. V. Vitt, Y. T. Struchkov, A. S. Balsanov, T. V. Timofeeva, V. A. Tsyrapkin, M. G. Ryzkov, L. A. Lysova, V. I. Bakhmutov, V. M. Belikov, J. Am. Chem. Soc. 1985, 107, 4252-4259.
19. [8c] D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761.
20. [8d] D. Seebach, E. Juaristi, D. D. Miller, C. Schickli, T. Weber, Helv. Chim. Acta 1987, 70, 237-261.
21. [8e] D. A. Evans, J. Am. Chem. Soc. 1987, 109, 7151-7157.
22. [8f] H. Kuzuhara, N. Watanabe, M. Ando, J. Chem. Soc., Chem. Commun. 1987, 95-96.
23. [8g] U. Schöllkopf, J. Bardenhagen, Liebigs Ann. Chem. 1987, 393-397.
24. [8h] D. Seebach, S. G. Müller, U. Gysel, J. Zimmermann, Helv. Chim. Acta 1988, 71, 1303-1318.
25. [8i] T. Owa, M. Otsuka, M. Ohno, Chem. Lett. 1988, 83-86.
26. [8j] G. Bold, R. O. Duthaler, M. Riediker, Angew. Chem. 1989, 101, 491-493;
27. Angew. Chem. Int. Ed. Engl. 1989, 28, 497-498.
28. [8k] S. Kanemasa, M. Takahashi, E. Wada, A. Tatsukawa, Tetrahedron Lett. 1993, 34, 677-680.
29. U. Kazmaier, Angew. Chem. 1994, 106, 1046-1047;
30. Angew. Chem. Int. Ed. Engl. 1994, 33, 998-999;
31. Tetrahedron 1994, 50, 12895-12902;
32. J. Org. Chem. 1994, 59, 6667-6670;
33. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213-2214;
34. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2014.
35. U. Kazmaier, R. Grandel, Synlett 1995, 945-946.
36. R. E. Ireland, A. K. Willard, Tetrahedron Lett. 1975, 3975-3978.
37. C. H. Heathcock, C. T. Buse, W. A. Kleschik, M. C. Pirrung, J. E. Sohn, J. Lampe, J. Org. Chem. 1980, 45, 1066-1081.
38. H. B. Mekelburger, C. S. Wilcox in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991, vol. 2, p. 101.
39. S. E. Denmark, B. R. Henke, J. Am. Chem. Soc. 1991, 113, 2177-2194.
40. P. Fellman, J. E. Dubois, Tetrahedron 1978, 34, 1349-1357.
41. C. H. Heathcock in Asymmetric Synthesis (Ed.: J. J. Morrison), Academic Press, New York, 1984, vol. 3, chapter 2.
42. C. H. Heathcock, M. C. Pirrung, S. D. Young, J. P. Hagen, E. T. Jarvi, U. Badertscher, H.-P. Märki, S. H. Montgomery, J. Am. Chem. Soc. 1984, 106, 8161-8174.
43. C. H. Heathcock in Modern Synthetic Methods (Ed.: R. Scheffold), Verlag Helvetica Chimica Acta, Basel, 1992, vol. 6, p. 36.
44. Further details of the crystal structure investigation are available on request from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-391004, the names of the authors and the journal citation.
45. E. Keller, SCHAKAL 92, Graphics Programm for Molecular and Crystallographic Models, Universität Freiburg, Germany, 1993.