Enantioconvergent transformation of racemic cis-dialkyl substituted epoxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9089-9092

  Bellucci, Giuseppe ^a   Chiappe, Cinzia ^a   Cordoni, Antonio ^a   Ingrosso, Giovanni ^b  

^a UNIVERSITY OF PISA   (Italy)

^b Dipartimento di Biologia   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; EPOXIDE HYDROLASE;

ARTICLE; CATALYSIS; DRUG PURITY; ENANTIOMER; HYDRATION; HYDROLYSIS; STEREOSPECIFICITY;

EID: 0030577481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02094-1     Document Type: Article

References (25)

1. 1. Schurig, V.; Betschnger, F. Chem. Rev. 1992, 92, 873. Sharpless, K. B. Chem. Rev. 1994, 94, 2583.
2. 1. Schurig, V.; Betschnger, F. Chem. Rev. 1992, 92, 873. Sharpless, K. B. Chem. Rev. 1994, 94, 2583.
3. 2. Besse, P; Veshambre, H. Tetrahedron, 1994, 50, 8885. de Bont, J. A. M. Tetrahedron: Asym. 1993, 4, 1331. Ader, U.; Schneider, M. P. Tetrahedron: Asym. 1992, 2, 1605.
4. 2. Besse, P; Veshambre, H. Tetrahedron, 1994, 50, 8885. de Bont, J. A. M. Tetrahedron: Asym. 1993, 4, 1331. Ader, U.; Schneider, M. P. Tetrahedron: Asym. 1992, 2, 1605.
5. 2. Besse, P; Veshambre, H. Tetrahedron, 1994, 50, 8885. de Bont, J. A. M. Tetrahedron: Asym. 1993, 4, 1331. Ader, U.; Schneider, M. P. Tetrahedron: Asym. 1992, 2, 1605.
6. 3. Mischitz, M.; Kroutil, W.; Wandel, U.; Faber, K. Tetrahedron: Asym. 1995, 6, 1261.
7. 4. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Tetrahedron 1996, 52, 4593.
8. 5. Blée, E.; Schuber, F. J. Biol. Chem. 1992, 267, 11881.
9. 6. Grahem, S. M.; Prestwich, G. D. J. Org. Chem. 1994, 59, 2956.
10. 7. Seidegard, J.-E.; DePierre, J. W. Biochem. Biophys. Acta 1983, 695, 251. Meijer, J.; De Pierre, J. W. Chem. Biol. Interact. 1988, 64, 207.
11. 7. Seidegard, J.-E.; DePierre, J. W. Biochem. Biophys. Acta 1983, 695, 251. Meijer, J.; De Pierre, J. W. Chem. Biol. Interact. 1988, 64, 207.
12. 8. Lacourciere, G. M.; Armstrong, R. N. J. Am. Chem. Soc. 1993, 115, 10466.
13. 9. Bellucci, G; Chiappe, C.; Ingrosso, G; Rosini, C. Tetrahedron: Asym. 1995, 6, 1911, and references cited therein.
14. 10. a) Bellucci, G; Capitani, I; Chiappe, C.; Marioni J. Chem. Soc. Chem. Commun. 1989, 1170.
15. b) Bellucci, G.; Chiappe, C.; Ingrosso, G. Chirality, 1994, 6, 577.
16. 11. Bellucci, G; Chiappe, C.; Conti, L.; Marioni, F.; Pierini, G. J. Org. Chem. 1989, 54, 5878, and references cited therein.
17. 12. Bellucci, G; Chiappe, Cordoni, A. Tetrahedron: Asym. 1996, 7, 197.
18. 2OH).
19. 2OH).
20. 15. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. J. Org. Chem. 1969, 34, 2543.
21. 16. A lower product enantioselectivity as been reported (Watabe, T.; Akamatsu, K. Biochim. Biophys. Acta 1972, 279, 297) for the mEH catalyzed hydrolysis of 1b determined on the basis of the optical rotation of the methyl ester of the product diol. However, optical rotation values for vicinal diols should be regarded with caution because they are very sensitive to traces of moisture.
22. D = 21.5 (methanol). Reported value (Mc Ghie, J. F.; Ross, W. A.; Spence, J. W.; James, F. J. Chem. Ind. 1972, 536) for (R,R)-2a 25.42.
23. D = 21.0 (methanol). Reported value (McGhie, J. F.; Ross, N. A.; Polton D. J. Chem. Ind. 1956, 353) for the methyl ester of (R,R)-2b, 22.52.
24. 18. Bellucci, G; Chiappe, Cordoni, A. Tetrahedron: Asym. 1993, 4, 1153.
25. 19. Eugster, H.-P.; Sengstag C.; Hinnen, A.; Meyer, U. A.; Würgler F. E.; Biochem. Pharm. 1991, 42, 1367.