Inversion of configuration of (S)-β-hydroxy-γ-butyrolactone with total retention of the enantiomeric purity

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 2705-2707

  De Angelis, Francesco ^a   De Fusco, Enrico ^b   Desiderio, Paola ^b   Giannessi, Fabio ^b   Piccirilli, Fabrizio ^b   Tinti, Maria Ornella ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b Sigma Tau SpA   (Italy)

Author keywords

Asymmetric synthesis; Chiral synthons; Configuration inversion; Hydroxy lactones; Lactones

Indexed keywords

ANTIBIOTIC AGENT; BETA HYDROXY GAMMA BUTYROLACTONE; HEXOSE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032742946     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2705::aid-ejoc2705>3.0.co;2-4     Document Type: Article

References (24)

1. [1a] O. Uchikawa, N. Okukado, T. Sakata, K. Arase, K. Terada, Bull. Chem. Soc. Jpn. 1988, 61, 2025-2029.
2. [1b] R. L. Hollingsworth, EP 513430, 1992; Chem. Abstr. 1993, 118, 168701 h.
3. [1b] R. L. Hollingsworth, EP 513430, 1992; Chem. Abstr. 1993, 118, 168701 h.
4. [1c] G. Calvisi, R. Catini, W. Chiariotti, F. Giannessi, S. Muck, M. O. Tinti, F. De Angelis, Synlett 1997, 71-74.
5. [1d] S. Hanessian, C. Girard, Synlett 1994, 861-862.
6. [1e] T. Suzuki, H. Idogaki, N. Kasai, Enzyme Microb. Technol. 1999, 24, 13-20.
7. [2a] M. Larcheveque, S. Henrot, Tetrahedron 1990, 46, 4277-4282.
8. [2b] B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh, C. Sih, J. Am. Chem. Soc. 1983, 105, 5925-5926.
9. [2c] T. Kaneko, R. Yoshida, Bull. Chem. Soc. Jpn. 1962, 35, 1153-1155.
10. H. Yamada, H. Sugiyama, M Kajiwara, Heterocycles 1987, 26, 2841-2844.
11. [4a] H.-M. Shie, G. D. Prestwich, Tetrahedron Lett. 1982, 23, 4643-4646.
12. [4b] K. Mori, T. Takigawa, T. Matsuo, Tetrahedron 1979, 35, 933-940.
13. [5a] Four steps (36%) from ethyl 4-chloro-3-oxo-butanoate, through enantioselective reduction with baker yeast: D. Seebach, M. Eberle, Synthesis 1986, 37-40.
14. [5b] Seven steps (29% ) from L-ascorbic acid: A. Tanaka, K. Yamashita, Synthesis 1987, 570-572.
15. 4: S. Saito, T. Hasegawa, M. Inaba, R. Nishida, T. Fujii, S. Nomizu, T. Moriwake, Chem. Lett. 1984, 1389-1392.
16. [6a] S. C. Stinson, Chem. Eng. News 1992, 70 (39), 46-79.
17. [6b] S. C. Stinson, Chem. Eng. News 1993, 71 (39), 38-65.
18. F. Giannessi, M. O. Tinti, F. De Angelis, (Sigma-Tau), RM97A000780.
19. M. Suzuki, GC-MS News 1985, 13, 41-44.
20. J. Kaulen, Angew. Chem. Int. Ed. Engl. 1987, 26, 773-774.
21. The synthesis of this compound has recently been reported, without analytical data and yields, as the first step in a patented process for the preparation of (R)-carnitine starting from 1: James R. McCarthy, (Neurocrine Biosciences), US 5473104, 1995; Chem. Abstr. 1996, 124, 233138v. In our hands, following this procedure, yields were disappointingly low.
22. The synthesis of this compound has recently been reported, without analytical data and yields, as the first step in a patented process for the preparation of (R)-carnitine starting from 1: James R. McCarthy, (Neurocrine Biosciences), US 5473104, 1995; Chem. Abstr. 1996, 124, 233138v. In our hands, following this procedure, yields were disappointingly low.
23. R. C. Anand, N. Selvapalam, Synth. Commun. 1994, 24, 2743-2747.
24. Details of the ee determination by GC will be published in a subsequent paper.