Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides

European Journal of Organic Chemistry

Volumn , Issue 23, 2001, Pages 4537-4542

  Mayer, Sandra F ^a   Steinreiber, Andreas ^a   Orru, Romano V A ^b   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Domino reaction; Enantioselectivity; Hydrolases; Umpolung

Indexed keywords

EPOXIDE; TETRAHYDROFURAN;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHIRALITY; CYCLIZATION; ENANTIOMER; LIPOPHILICITY; REACTION ANALYSIS;

EID: 0035214113     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.0.co;2-e     Document Type: Article

References (18)

1. R. A. Bunce, Tetrahedron 1995, 51, 13103-13159.
2. W. Kroutil, S. F. Mayer, K. Faber, in: The Fourth International Electronic Conference on Synthetic Organic Chemistry" (EC-SOC-4) (Eds.: T. Wirth, C. O. Kappe, E. Felder, U. Diedrichsen, S.-K. Lin), paper no. C0019, MPDI, 2000, CD-ROM edition, ISBN 3-906980-05-7.
3. W. Kroutil, M. Mischitz, K. Faber, J. Chem. Soc., Perkin Trans. 1 1997, 3629-3636.
4. U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107-117.
5. For substrates bearing alkene or alkyne moieties see: I. Osprian, W. Stampfer, K. Faber, J. Chem. Soc., Perkin Trans. 1 2000, 3779-3785.
6. For substrates bearing masked hydroxy groups see: A. Steinreiber, I. Osprian, S. F. Mayer, R. V. A. Orru, K. Faber, Eur. J. Org. Chem. 2000, 3703-3711.
7. For a preliminary communication see: S. F. Mayer, A. Steinreiber, R. V. A. Orru, K. Faber, Tetrahedron: Asymmetry 2001, 12, 41-43.
8. G. B. Payne, J. Org. Chem. 1962, 27, 3819-3822.
9. A related enzyme-triggered transformation of a haloepoxide catalyzed by microsomal epoxide hydrolase has been reported: G. Bellucci, G. Berti, M. Ferretti, F. Marioni, F. Re, Biochem. Biophys. Res. Commun. 1981, 102, 838-844. However, the stereochemical course of this reaction was not investigated.
10. J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734-736.
11. [11a] M. Nardini, R. Rink, D. B. Janssen, B. W. Dijkstra, J. Mol. Catal. B 2000, 11, 1035-1042;
12. [11b] R. Rink, M. Fennema, M. Smids, U. Dehmel, D. B. Janssen, J. Biol. Chem. 1997, 272, 14650-1467.
13. It should be noted that a second switch of CIP priority occurs for the resulting intermediates during the cyclisation step.
14. K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, Tetrahedron Lett. 1994, 35, 3469-3472.
15. W. Kroutil, I. Osprian, M. Mischitz, K. Faber, Synthesis 1997, 156-158.
16. I. Osprian, W. Kroutil, M. Mischitz, K. Faber, Tetrahedron: Asymmetry 1997, 8, 65-71.
17. M. Mischitz, W. Kroutil, U. Wandel, K. Faber, Tetrahedron: Asymmetry 1995, 6, 1261-1272.
18. W. Krenn, I. Osprian, W. Kroutil, G. Braunegg, K. Faber, Biotechnol. Lett. 1999, 21, 687-690.