Stereoselective amination of 5-substituted γ-lactones and γ-lactams - A convenient route for the preparation of 5-substituted (3S,5S)-3- acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-acetylaminopyrrolidin-2-ones

European Journal of Organic Chemistry

Volumn , Issue 7, 1999, Pages 1581-1584

  Škof, Marko ^a   Svete, Jurij ^a   Kmetič, Matej ^a   Golič Grdadolnik, Simona ^b   Stanovnik, Branko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

Aminations; Asymmetric synthesis; Nitrosations; Pyrrolidin 2 ones; Tetrahydrofuran 2 ones

Indexed keywords

GAMMA LACTAM DERIVATIVE; GAMMA LACTONE DERIVATIVE; PYRROLIDINE DERIVATIVE; TETRAHYDRO 2 FURANONE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0342452329     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199907)1999:7<1581::AID-EJOC1581>3.0.CO;2-2     Document Type: Article

References (26)

1. O. Touster, Org. React. 1953, 7, 327-377.
2. H. Bredereck, G. Simchen, Angew. Chem. 1963, 75, 1102.
3. H. Bredereck, G. Simchen, G. Beck, Liebigs Ann. Chem. 1972, 762, 62-72.
4. H. Bredereck, G. Simchen, W. Griebenow, Chem. Ber. 1974, 107, 1545-1554.
5. R. F. Abdulla, E. S. Brinkmeyer, Tetrahedron 1979, 35, 1675-1735.
6. For short reviews see: [6a] B. Stanovnik, "Methyl 2-Benzoyl-amino-3-dimethylaminopropenoate in the Synthesis of Heterocyclic Systems" in Progress in Heterocyclic Chemistry (Eds.: H. Suschitzky, E. F.V. Scriven), Pergamon Press, Oxford, 1993, vol. 5, pp. 34-53.
7. [6b] B. Stanovnik, Molecules 1996, 1, 123-127.
8. For recent publications see: [7a] L. Selič, S. Golič-Grdadolnik, B. Stanovnik, Helv. Chim. Acta 1997, 80, 2418-2425.
9. [7b] J. Smodiš, B. Stanovnik, Tetrahedron 1998, 54, 9799-9810.
10. [7c] L. Pizzioli, B. Ornik, J. Svete, B. Stanovnik, Helv. Chim. Acta 1998, 81, 231-235.
11. [7d] L. Selič, B. Stanovnik, Helv. Chim. Acta 1998, 81, 1634-1639.
12. [7e] L. Selič, S. Strah, R. Toplak, B. Stanovnik, Heterocycles 1998, 47, 1017-1022.
13. [7f] M. Škof, J. Svete, B. Stanovnik, L. Golič, S. Golič-Grdadolnik, L. Selič, Helv. Chim. Acta 1998, 81, 2332-2340.
14. M. Kmetič, B. Stanovnik, J. Heterocycl. Chem. 1995, 32, 1563-1565.
15. M. Kmetič, B. Stanovnik, J. Heterocycl. Chem. 1997, 34, 1705-1708.
16. For the synthesis of some α-amino-γ-hydroxy and α,γ-diamino compounds see: [10a] H. Hahn, H. Heitsch, R. Rathmann, G. Zimmermann, C. Bormann, H. Zähner, W. A. König, Liebigs Ann. Chem. 1987, 803-807.
17. [10b] N. G. Park, S. Lee, H. Maeda, H. Aoyagi, T. Kato, Bull. Chem. Soc. Jpn. 1989, 62, 2315-2319.
18. [10c] B. J. Williams, P. D. Leeson, G. Hannah, R. Baker, J. Chem. Soc., Chem. Commun. 1989, 1740-1742.
19. [10d] J. Ariza, J. Font, R. M. Ortuño, Tetrahedron 1990, 46, 1931-1942.
20. [10e] A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 1991, 56, 1894-1901.
21. [10f] R. F. W. Jackson, A. B. Rettie, Tetrahedron Lett. 1993, 34, 2985-2986.
22. [10g] C. Schmeck, L. Hegedus, J. Am. Chem. Soc. 1994, 116, 9927-9934.
23. [10h] V. Jäger, R. Müller, T. Leibold, M. Hein, M. Schwarz, M. Fengler, L. Jaroskova, M. Pätzel, P.-Y. LeRoy, Bull. Soc. Chim. Belg. 1994, 103, 491-507.
24. S. Saijo, M. Wada, J.-I. Himizu, A. Ishida, Chem. Pharm. Bull. 1980, 28, 1449-1458.
25. O. Cervinka, L. Hub, Coll. Czech. Chem. Commun. 1968, 33, 2927-2932.
26. M. Taniguchi, K. Koga, S. Yamada, Tetrahedron 1974, 30, 3547-3552.