Synthesis and asymmetric hydrogenation of 3,5-dioxoheptanedioates. Preparation of enantiomerically pure substituted δ-valerolactones

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4959-4963

  Kiegiel, Jaroslaw ^a   Jóźwik, Julita ^a   Woźniak, Krzysztof ^a   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; PIMELIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343061079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00747-4     Document Type: Article

References (27)

1. (a) Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346;
2. (b) Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 1165.
3. Pettit, G. R.; Cichacz, Z. A., Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302.
4. Mishima, H.; Kurobayashi, C.; Tamura, S.; Sato, S.; Kuwano, H.; Saito, A. Tetrahedron Lett. 1975, 711.
5. Albers-Schönberg, G.; Arison, B. H.; Chabala J. C.; Douglas, A. W.; Eskola, P.; Fisher, M. H.; Lusi, A.; Mrozik, H.; Smith, J. L.; Tolman, R. L. J. Am. Chem. Soc. 1981, 103, 4216.
6. (a) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126;
7. (b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422;
8. (c) Molinski, T. F. Tetrahedron Lett. 1996, 37, 7879.
9. For recent syntheses and applications of chiral 3-hydroxy-5-substituted-δ-valerolactones, see: (a) Dunkel, R.; Mentzel, M. Tetrahedron 1997, 53, 14929; (b) Kaku, H.; Tanaka, M.; Norimine, Y.; Miyashita, Y.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1997, 8, 195; (c) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 5, 797; (d) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905, and references cited therein.
10. For recent syntheses and applications of chiral 3-hydroxy-5-substituted-δ-valerolactones, see: (a) Dunkel, R.; Mentzel, M. Tetrahedron 1997, 53, 14929; (b) Kaku, H.; Tanaka, M.; Norimine, Y.; Miyashita, Y.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1997, 8, 195; (c) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 5, 797; (d) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905, and references cited therein.
11. For recent syntheses and applications of chiral 3-hydroxy-5-substituted-δ-valerolactones, see: (a) Dunkel, R.; Mentzel, M. Tetrahedron 1997, 53, 14929; (b) Kaku, H.; Tanaka, M.; Norimine, Y.; Miyashita, Y.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1997, 8, 195; (c) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 5, 797; (d) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905, and references cited therein.
12. For recent syntheses and applications of chiral 3-hydroxy-5-substituted-δ-valerolactones, see: (a) Dunkel, R.; Mentzel, M. Tetrahedron 1997, 53, 14929; (b) Kaku, H.; Tanaka, M.; Norimine, Y.; Miyashita, Y.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1997, 8, 195; (c) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 5, 797; (d) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905, and references cited therein.
13. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
14. Stachel, H.-D. Angew. Chem. 1957, 69, 507.
15. (a) Stachel, H.-D. Archiv. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735;
16. (b) Stachel, H.-D.; Jungkenn, M.; Koser-Gnoss, C.; Poschenrieder, H.; Redlin, J. Liebigs. Ann. Chem. 1994, 9, 961.
17. (a) Beranek, J.; Smrt, J.; Šorm, F. Collect. Czech. Chem. Commun. 1954, 19, 1231;
18. (b) Smrt, J.; Beranek, J.; Šorm, F. Collect. Czech. Chem. Commun. 1955, 20, 285;
19. (c) Šorm, F.; Beranek, J.; Smrt, J.; Sicher, J. Collect. Czech. Chem. Commun. 1955, 20, 593;
20. (d) Polczynski, P.; Paul, H. J. Prakt. Chem. 1970, 312, 240.
21. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431.
22. 3)
23. Shao, L.; Kawano, H.; Saburi, M.; Uchida, Y. Tetrahedron 1993, 49, 1997.
24. Oppolzer, W. Tetrahedron 1987, 43, 1969.
25. 3).
26. 3, 125 MHz) δ 37.2, 39.3, 40.0, 52.1, 63.6, 73.2, 169.8, 170.1.
27. Bac, N. V.; Langlois, Y. Tetrahedron Lett. 1988, 29, 2819.