Selective acylations of multifunctional nucleophiles, including carbohydrates and nucleosides, with intermediates generated by Wolff rearrangement of amino acid derived diazo ketones: Preparation of β-amino acid derivatives

Liebigs Annales

Volumn , Issue 7, 1996, Pages 1121-1129

  Guibourdenche, Christel ^a   Podlech, Joachim ^a,b   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

5 Nucleoside esters of (3 S) 3 aminocarboxylic acids; Adenosin; Arndt Eistert homologation of amino acids; Deoxyadenosin; Thymidin; Wolff rearrangement; Amino acid esters of xylose and sucrose

Indexed keywords

EID: 33749138438     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960710     Document Type: Article

References (52)

1. D. F. Rane, V. M. Girijavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena, A. T. McPhail, Tetrahedron Lett. 1993, 34, 3201-3204;
2. S. Nomoto, T. Teshima, T. Wakamiya, T. Shiba, Tetrahedron 1978, 34, 921-927;
3. H. Onuki, K. Tachibana, N. Fusetani, Tetrahedron Lett. 1993, 34, 5609-5612;
4. L. Yang, A. E. Weber, W. J. Greenlee, A. Patchett, Tetrahedron Lett. ibid. 1993, 34, 7035-7038.
5. C. N. C. Drey in Chemistry and Biochemistry of Amino Acids (Ed.: G. C. Barrett), Chapman and Hall, London, 1985, p. 25-54;
6. H. Sone, T. Nemoto, H. Ishiwata, M. Ojika, K. Yamada, Tetrahedron Lett. 1993, 34, 8449-8452.
7. Reviews: K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38-69;
8. Angew. Chem. Int. Ed. Engl. 1994, 33, 45-66.
9. Total synthesis: R. A. Holten, H.-B. Kim, C. Somoza, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile, J. H. Liu, J. Am. Chem. Soc. 1994, 116, 1599-1600;
10. K. C. Nicolaou, H. Ueno, J.-J. Liu, P. G. Nantermet, Z. Yang, J. Renaud, K. Paulvannan, R. Chadha, J. Am. Chem. Soc. ibid. 1995, 117, 653-659, and reference cited therein.
11. The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie Academic & Professional, London, 1992, and citations on p. 346.
12. R. M. Williams, Synthesis of Optically Active α-amino Acids, Pergamon Press, Oxford, 1989;
13. R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650.
14. F. Arndt, B. Eistert, W. Partale, Ber. Dtsch. Chem. Ges. 1927, 60, 1364-1370;
15. T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091-1160.
16. L. Wolff, Justus Liebigs Ann. Chem. 1912, 394, 23-36;
17. H. Meier, K.-P. Zeller, Angew. Chem. 1975, 87, 52-63;
18. Angew. Chem. Int. Ed. Engl. 1975, 14, 32-43.
19. K. Balenović, I. Jambresić, B. Gašpert, D. Cerar, Recl. Trav. Chim. Pays-Bas 1956, 75, 1252-1258;
20. K. Balenović, N. Stimac, Croat. Chem. Acta 1957, 29, 152-156, and references cited therein.
21. D. S. Tarbell, J. A. Price, J. Org. Chem. 1957, 22, 245-250.
22. L. Baláspiri, B. Penke, G. Papp, G. Dombi, K. Kovács, Helv. Chim. Acta 1970, 53, 969-973.
23. [13a] G. Stork, Y. Nakahara, Y. Nakahara, W. J. Greenlee, J. Am. Chem. Soc. 1978, 100, 7775-7777.
24. [13b] J. Cooper, P. T. Gallagher, D. W. Knight, J. Chem. Soc., Chem. Commun. 1988, 509-510.
25. [13c] P. A. Grieco, Y. S. Hon, A. Perez-Medrano, J. Am. Chem. Soc. 1988, 110, 1630-1631.
26. [13d] C. W. Jefford, Q. Tang, A. Zaslona, J. Am. Chem. Soc. 1991, 113, 3513-3518.
27. [13e] Y. Ikeda, D. Ikeda, S. Kondo, J. Antibiot. 1992, 45, 1677-1680.
28. [13f] D. A. Evans, S. J. Miller, M. D. Ennis, J. Org. Chem. 1993, 58, 471-485.
29. J. Podlech, D. Seebach, Liebigs Ann. 1995, 1217-1228.
30. J. Podlech, D. Seebach, Angew. Chem. 1995, 107, 507-509;
31. Angew. Chem. Int. Ed. Engl. 1995, 34, 471-472.
32. 1H-NMR spectroscopy. There is no evidence for mutual rearrangement of the regioisomers by acyl shift.
33. See the zip reaction: M. Hesse, Ring Enlargement in Organic Chemistry, VCH, Weinheim, 1991, p. 97-110.
34. A kind of "zip reaction" does definitely not occur during the purification of the product mixture as, after benzoylation of the crude mixture, the corresponding N-benzoylated ester could not be detected in the NMR spectra.
35. In the case of the adducts formed with 2-(methylamino)ethanol, the yields dropped significantly (from quantitative to 65%) when the reaction times were increased from 3 to 18 h. Also, the ratio of the two regioisomers was shifted somewhat during chromatography.
36. For reviews on "atom economic reactions" see: B. M. Trost, Angew. Chem. 1995, 107, 285-307;
37. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
38. B. M. Trost, Science 1991, 1471
39. . For thoughts on future challenges in organic synthesis see: D. Seebach, Angew. Chem. 1990, 102, 1363-1409;
40. Angew. Chem. Int. Ed. Engl., 1990, 29, 1320-1367.
41. C. Chauvin, K. Baczko, D. Plusquellec, J. Org. Chem. 1993, 58, 2291-2295;
42. C. Chauvin, D. Plusquellec, Tetrahedron Lett. 1993, 32, 3495-3498;
43. P. Uhlmann, A. Vasella, Helv. Chim. Acta 1994, 77, 1175-1192;
44. P. Reddy Maddusani, E. Bozó, B. Bernet, A. Vasella, Helv. Chim. Acta ibid. 1994, 77, 257-290;
45. P. Reddy Maddusani, B. Bernet, A. Vasella, Helv. Chim. Acta ibid. 1994, 77, 334-350.
46. D. C. Johnson in Cellulose Chemistry and its Application (Eds.: T. P. Nevell, S. H. Zeronian), Wiley, New York, 1985, p. 181-201.
47. D. Seebach, A. K. Beck, A. Studer in Modern Synthetic Methods 1995 (Eds.: B. Ernst, C. Leumann), VCH, Weinheim, 1995, vol. 7, p. 1-178.
48. The presence of the a lithium salt proved to have no effect on the yields and selectivities found in this reaction, but the improved solubility of the sugar (vide supra) made its use as an additive advantageous.
49. S. Chladek in Chemistry of Nucleosides and Nucleotides (Ed.: L. B. Townsend), Plenum Press, New-York, 1995, vol. 3, p. 107.
50. M. Ghosh, M. J. Miller, Bioorg. Med. Chem. 1995, 3, 1519.
51. Eur. J. Biochem. 1984, 138, 9-37.
52. J. Podlech, D. Seebach, Helv. Chim. Acta 1995, 78, 1238-1246.