Lipase-catalyzed second-order asymmetric transformations as resolution and synthesis strategies for chiral 5-(acyloxy)-2(5H)-furanone and pyrrolinone synthons

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3801-3803

  Van Der Deen, Hanneke ^a   Cuiper, Agnes D ^a   Hof, Robert P ^a   Van Oeveren, Arjan ^a   Feringa, Ben L ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PYRROLINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER;

EID: 0029930761     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953812h     Document Type: Article

References (21)

1. (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York. 1994; p 414.
2. (b) Morrison, J. D. Asymmetric Synthesis: Academic Press: New York. 1983: Vol. 1, p 3.
3. For a review of second-order asymmetric transformations (dynamic kinetic resolutions), see: Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
4. Fulling, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 109, 2845.
5. (a) Gu, R. L.; Lee, I. S.; Sih, C. J. Tetrahedron Lett. 1992, 33, 1953.
6. (b) Bevinakatti, H. S.; Newadkar, R. V.; Banerji, A. A. J. Chem. Soc., Chem. Commun. 1990, 1091.
7. Tan, D. S ; Gunter, M. M.; Drueckhammer, D. G. J Am. Chem. Soc. 1995, 117, 9093.
8. Oeveren van, A.; Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1994, 59, 5999.
9. (a) Middel, O.; Woerdenbag, H. J.; Uden van, W. A.; Oeveren van, A.; Jansen, J. F. G. A.; Feringa, B. L.; Konnigs, A. W. T.; Pras, N.; Kellogg, R. M. J. Med. Chem. 1995, 38, 2112.
10. (b) Thuring, J. W. J. F.; Nefkens, G. H. L.; Schaafstra, R.; Zwanenburg, B. Tetrahedron 1995, 51, 5047.
11. (a) Feringa, B. L.; Lange de, B.; Jong de, J. C. J. Org. Chem. 1989, 54, 2471.
12. (b) Toda, F.; Tanaka, K.; Leung, C. W.; Meetsma, A.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1994, 2371.
13. (c) Feringa, B. L.; Lange de, B. Tetrahedron 1988, 44, 7213.
14. (d) Faber, W. S.; Kok, J.; Lange de, B.; Feringa, B. L. Tetrahedron 1994, 50, 4775.
15. Koot, W. J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059. For application in the synthesis of (-)-peduncularine, see: Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 11, 2588.
16. Koot, W. J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059. For application in the synthesis of (-)-peduncularine, see: Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 11, 2588.
17. Deen van der, H.; Hof, R. P.; Oeveren van, A.; Feringa, B. L.; Kellogg, R. M. Tetrahedron Lett. 1994, 45, 8441.
18. The absolute configuration of (+)-1a is thought to be S as illustrated. This is based on correlations carried out with the corresponding (+)-1b. Briefly. Diels - Alder cycloaddition with cyclopentadiene proceeds in the expected endo fashion and on the face of the alkene opposite the acyloxy group. Transacetalization of this cycloadduct either with methanol or with water leads to two adducts identical to those obtained from the cycloaddition followed by analogous transacetalization of (5R)-3 except that the optical rotations are opposite. The configuration of (+)-1b is therefore S and (+)-1a also S by analogy.
19. The lipase does not catalyze ring-opening of the lactone at a detectable rate.
20. Bovara, R.; Carrera, G.; Ferrara, L.; Riva, S. Tetrahedron: Asymmetry 1991, 2, 931.
21. The absolute configuration is indicated as analogous to 1; this remains to be proven.