Modifications of peptides by chelate claisen rearrangements of manganese enolates

European Journal of Organic Chemistry

Volumn , Issue 7, 2000, Pages 1241-1251

  Maier, Sabine ^a   Kazmaier, Uli ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Amino acids; Claisen rearrangements; Enolates; Metal complexes; Peptides

Indexed keywords

ALCOHOL; ALLYL COMPOUND; ALUMINUM; AMINO ACID; CHELATE; COBALT CHLORIDE; MAGNESIUM CHLORIDE; MANGANESE CHLORIDE; MANGANESE DERIVATIVE; METAL COMPLEX; PEPTIDE; TIN CHLORIDE; TITANIUM; ZINC CHLORIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; CONFORMATION; PROTEIN MODIFICATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0034051951     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1241::AID-EJOC1241>3.0.CO;2-U     Document Type: Article

References (51)

1. Amino Acids, Peptides and Proteins, Specialist Periodical Reports, Chem. Soc., London.
2. U. Gräfe, Biochemie der Antibiotika, Spektrum, Heidelberg, 1992.
3. [3a] E. Mutschier, Arzneimittelwirkungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1991.
4. [3b] A. E. Eberle, Chimia 1991, 45, 145-153.
5. [4a] J.-C. Gfeller, A. K. Beck, D. Seebach, Helv. Chim. Acta 1980, 63, 728-732.
6. [4b] M. J. Dunn, S. Gomez, R. F. W. Jackson, J. Chem. Soc., Perkin Trans. 1 1995, 1639-1640.
7. [4c] J. Barluenga, M. A. García-Martín, J. M. González, P. Clapés, G. Valencia, Chem. Commun. 1996, 1505-1506.
8. [4d] M. Mezzetti, E. Mincione, R. Saladino, Chem. Commun. 1997, 1063-1064.
9. T. Pietzonka, D. Seebach, Angew. Chem. 1992, 104, 1543-1545; Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1483.
10. T. Pietzonka, D. Seebach, Angew. Chem. 1992, 104, 1543-1545; Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1483.
11. D. Seebach, S. Y. Ko, H. Kessler, M. Köck, M. Reggelin, P. Schmieder, M. D. Walkinshaw, J. J. Bölsterli, D. Bevec, Helv. Chim. Acta 1991, 74, 1953-1990.
12. [7a] C. J. Easton, I. M. Scharfbillig, E. W. Tan, Tetrahedron Lett. 1988, 29, 1565-1568.
13. [7b] G. Apitz, W. Steglich, Tetrahedron Lett. 1991, 32, 3163-3166.
14. [7c] W. Steglich, M. Jäger, S. Jaroch, P. Zistler, Pure Appl. Chem. 1994, 66, 2167-2170.
15. Reviews on selective alkylation of peptides: [8a] D. Seebach, Angew. Chem. 1988, 100, 1685-1715; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624.
16. Reviews on selective alkylation of peptides: [8a] D. Seebach, Angew. Chem. 1988, 100, 1685-1715; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624.
17. [8b] D. Seebach, Aldrichim. Acta 1992, 25, 59-66.
18. [8c] D. Seebach, A. K. Beck, A. Studer, in: Modern Synthetic Methods, vol. 7 (Eds.: B. Ernst, C. Leumann), Helvetica Chimica Acta/VCH, Basel/Weinheim, 1995, p. 1-178.
19. [9a] S. A. Miller, S. L. Griffiths, D. Seebach, Helv. Chim. Acta 1993, 76, 563-595.
20. [9b] D. Seebach, A. K. Beck, H. G. Bossler, C. Gerber, S. Y. Ko, C. W. Murtiashaw, R. Naef, S.-I. Shoda, A. Thaler, M. Krieger, R. Wenger, Helv. Chim. Acta 1993, 76, 1564-1590.
21. Review: U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295, and references cited therein.
22. U. Kazmaier, Angew. Chem. 1994, 106, 1046-1047; Angew. Chem. Int. Ed. Engl. 1994, 33, 998-999.
23. U. Kazmaier, Angew. Chem. 1994, 106, 1046-1047; Angew. Chem. Int. Ed. Engl. 1994, 33, 998-999.
24. [12a] U. Kazmaier, C. Schneider, Synlett 1996, 975-977.
25. [12b] U. Kazmaier, C. Schneider, Synthesis 1998, 1321-1326.
26. U. Kazmaier, J. Org. Chem. 1994, 59, 6667-6670.
27. B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557; Angew. Chem. Int. Ed. Engl. 1978, 17, 522-523.
28. B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557; Angew. Chem. Int. Ed. Engl. 1978, 17, 522-523.
29. [15a] F. L. Zumpe, U. Kazmaier, Synlett 1998, 1199-1200.
30. [15b] F. L. Zumpe, U. Kazmaier, Synthesis 1999, 1785-1791.
31. U. Kazmaier, S. Maier, Org. Lett., in press.
32. H. A. Staab, Liebigs Ann. 1957, 609, 75-83.
33. F. Weygand, U. Glöckler, Chem. Ber. 1956, 89, 653-656.
34. Better results are obtained with tosylated peptides: U. Kazmaier, S. Maier, J. Org. Chem. 1999, 64, 4574-4575.
35. Reactions of manganese enolates: [20a] M. T. Reetz, H. Haning, Tetrahedron Lett. 1993, 34, 7395-7398.
36. [20b] G. Cahiez, K. Chau, P. Cléry, Tetrahedron Lett. 1994, 35, 3069-3072.
37. If Tfa is used as a protecting group, LHMDS should be employed instead of LDA.
38. Determined by HPLC.
39. The term "simple diastereoselectivity" refers to the ratio of diastereomers with different relative configurations at the newly formed stereogenic centers (antilsyn). The simple diastereoselectivity describes the stereochemical outcome of the Claisen rearrangement and is strongly dependent on the discrimination of the transition states involved. The term "induced diastereoselectivity" refers to the ratio of diastereomers with different configurations at the stereogenic α-centers. It reflects the influence of a stereogenic center in the peptide chain on the formation of a new α-stereogenic center during the rearrangement. For a more detailed discussion, see: G. Helmchen in: Houben-Weyl: Methods of Organic Synthesis - Stereoselective Synthesis (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart. 1996, p. 53-56.
40. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213-2214; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2013 The pseudoenantiomeric quinidine provides the corresponding (S)-amino acid.
41. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213-2214; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2013 The pseudoenantiomeric quinidine provides the corresponding (S)-amino acid.
42. C. Schneider, U. Kazmaier, Synthesis 1998, 1314-1320.
43. H. J. Gais in: Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), VCH, Weinheim, 1995, p. 165-271.
44. LDA can also be used, but yields are slightly better with LHMDS.
45. [28a] C. Toniolo, M. Crisma, S. Pegoraro, G. Valle, G. M. Bonora, E. L. Becker, S. Polinelli, W. H. J. Boesten, H. E. Schoemaker, E. M. Meijer, J. Kamphuis, R. Freer, Peptide Res. 1991, 4, 66-71.
46. [28b] R. T. Shuman, R. B. Rothenberger, C. S. Campbell, G. F. Smith, D. S. Gifford-Moore, J. W. Paschal, P. D. Gesellchen, J. Med. Chem. 1995, 38, 4446-4453.
47. [29a] C. Palomo, J. M. Aizpurua, R. Urchegui, J. M. Garcia, J. Chem. Soc., Chem. Commun. 1995, 2327-2328.
48. [29b] L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 1996, 29, 268-274.
49. [29c] D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem 1996, 61, 4080-4086.
50. [29d] C. B. Bucher, H. Heimeartner, Helv. Chim. Acta 1996, 79, 1903-1915.
51. [29e] D. H. R. Barton, J. A. Ferreira, Tetrahedron 1996, 52, 9367-9386.