Dynamic kinetic resolution of secondary diols via coupled ruthenium and enzyme catalysis

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5237-5240

  Persson, B Anders ^a   Huerta, Fernando F ^b   Bäckvall, Jan E ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; ALCOHOL DERIVATIVE; ENZYME; RUTHENIUM;

ACYLATION; ARTICLE; CATALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033001550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990447u     Document Type: Article

References (34)

1. (a) Larsson, A. L. E.; Persson, B. A.; Bäckvall, J. E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1211.
2. (b) Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Bäckvall, J. E. J. Am. Chem. Soc. 1999, 121, 1645.
3. 2-symmetric auxiliaries and ligands in asymmetric synthesis, see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
4. (a) Short, R. P.; Kennedy, R. M.; Masamune, S. J. Org. Chem. 1989, 54, 1755.
5. (b) Zwaagstra, M. E.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1993, 4, 2163.
6. (c) Kim, M.-J.; Lee, I. S. Synlett 1993, 767.
7. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
8. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
9. (a) Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J. Org. Chem. 1998, 63, 4532.
10. (b) Otten, S.; Fröhlich, R.; Haufe, G. Tetrahedron: Asymmetry 1998, 9, 189.
11. 12 and tetraphenyl cyclopentadienone: Shvo, Y.; Menashe, N. Organometallics 1991, 10, 3885. For a modified procedure, see ref 1b.
12. For studies on enzymatic kinetic resolutions of diols, see: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1893, 4, 925. (b) Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 58, 6483. (c) Nagai, H.; Moromoto, T.; Achiwa, K. Synlett 1994, 289. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657. (e) Wallace, J. S.; Baldwin, B. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
13. For studies on enzymatic kinetic resolutions of diols, see: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1893, 4, 925. (b) Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 58, 6483. (c) Nagai, H.; Moromoto, T.; Achiwa, K. Synlett 1994, 289. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657. (e) Wallace, J. S.; Baldwin, B. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
14. For studies on enzymatic kinetic resolutions of diols, see: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1893, 4, 925. (b) Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 58, 6483. (c) Nagai, H.; Moromoto, T.; Achiwa, K. Synlett 1994, 289. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657. (e) Wallace, J. S.; Baldwin, B. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
15. For studies on enzymatic kinetic resolutions of diols, see: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1893, 4, 925. (b) Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 58, 6483. (c) Nagai, H.; Moromoto, T.; Achiwa, K. Synlett 1994, 289. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657. (e) Wallace, J. S.; Baldwin, B. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
16. For studies on enzymatic kinetic resolutions of diols, see: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1893, 4, 925. (b) Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 58, 6483. (c) Nagai, H.; Moromoto, T.; Achiwa, K. Synlett 1994, 289. (d) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657. (e) Wallace, J. S.; Baldwin, B. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231.
17. Removal of the meso isomer before enzymatic resolution, which increases the theoretical yield to 50%, has been reported; see ref 7d.
18. Using 4-chlorophenyl acetate as acyl donor under these conditions (160 mg enzyme/mmol substrate) gave (R,R)-3/meso-3 (80/20) in 55% yield after 1.5 h.
19. It was possible to separate the two diastereomers, (R,R)-5 and meso-5, by flash chromatography.
20. Micheli, R. A.; Hajos, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. J. Org. Chem. 1975, 40, 675
21. It was not possible to separate the enantiomers of diacetate 7 or diol 6 by HPLC or GC using the chiral columns specified in the general Experimental Section. Derivatization to the bis-2-chlorobenzoic acid ester or mono- or bis-benzyl ether prior to chromatographic analysis did not improve the separation.
22. (a) Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279.
23. (b) Boga, C.; Manescalchi, F.; Savoia, D. Tetrahedron 1994, 50, 4709.
24. In this case, the cyclization was carried out at a higher temperature (65 °C); see ref 3b.
25. Bäckvall, J. E.; Andreasson, U. Tetrahedron Lett. 1993, 34, 5459. See also: Trost, B. M.; Kulawiec, R. J. Tetrahedron Lett. 1991, 32, 3039.
26. Bäckvall, J. E.; Andreasson, U. Tetrahedron Lett. 1993, 34, 5459. See also: Trost, B. M.; Kulawiec, R. J. Tetrahedron Lett. 1991, 32, 3039.
27. Sablong, R.; Newton, C.; Dierkes, P.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 4933.
28. (a) Dubois, L.; Fiaud, J.-C.; Kagan, H. B. Tetrahedron 1995, 51, 3803.
29. (b) Zhang, H.-C.; Harris, B. D.; Costanzo, M. J.; Lawson, E. C.; Maryanoff, C. A.; Maryanoff, B. E. J. Org. Chem. 1998, 63, 7964.
30. Liu, K. K.-C.; Nozaki, K.; Wong, C.-H. Biocatalysis 1990, 3, 169.
31. An observation where the rate of the first acylation of the slow reacting S,S isomer of diol 4 is of the same magnitude as the second acylation of the fast reacting R,R isomer in a lipase catalyzed kinetic resolution has been reported: Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4942.
32. The (S,S)-4 isomer has been shown to be almost totally unreactive toward acylation using lipase from C. antarctica; see ref 7a.
33. Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
34. Itoh, O.; Ichikawa, Y.; Katano, H.; Ichikawa, K. Bull. Chem. Soc. Jpn. 1976, 49, 1353.