Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation-hydrolytic kinetic resolution sequence

Tetrahedron Asymmetry

Volumn 8, Issue 23, 1997, Pages 3927-3933

  Brandes, Bridget D ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLOROSTYRENE OXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; EPOXIDATION; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0031465950     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00568-5     Document Type: Article

References (47)

1. (a) 3-Benzyloxy: Britten, A. Z. Chemistry and Industry 1968, 771-772.
2. (b) 4-Benzyloxy-3-nitro: Hett, R.; Fang, Q. K.; Gao, Y.; Hong, Y.; Butler, H. T.; Nie, X.; Wald, S. A. Tetrahedron Lett. 1997, 38, 1125-1128.
3. (c) 4-Chloro: Nankai, M.; Nicholas, C.; Fage, D.; Carter, C. Br. J. Pharmacol. 1994, 112; PU142: Di Fabio, R.; Pietra, C.; Thomas, R. J.; Ziviani, L. Bioorg. Med. Chem. Lett. 1995, 5, 551-554.
4. (c) 4-Chloro: Nankai, M.; Nicholas, C.; Fage, D.; Carter, C. Br. J. Pharmacol. 1994, 112; PU142: Di Fabio, R.; Pietra, C.; Thomas, R. J.; Ziviani, L. Bioorg. Med. Chem. Lett. 1995, 5, 551-554.
5. (d) 3,4-Dichloro: Solladié-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494-3498 (also 2-naphthal).
6. (e) 4-Fluoro: Nieduzak, T. R.; Margolin, A. L. Tetrahedron: Asymmetry 1991, 2, 113-122.
7. (f) 3-Nitro: Wierenga, W.; Harrison, A. W.; Evans, B. R.; Chidester, C. G. J. Org. Chem. 1984, 49, 438-442.
8. (g) 4-Nitro: Marmo, E.; Caputi, A. P.; Rossi, F.; Lampa, E.; Vacca, C.; Brita, G.; Saini, R.-K.; Di Nola, R. Agressologie 1976, 17, 279-295. Pedragosa-Moreau, S.; Morisseau, C.; Baratti, J.; Zylber, J.; Archelas, A.; Furstoss, R. Tetrahedron 1997, 53, 9707-9714.
9. (g) 4-Nitro: Marmo, E.; Caputi, A. P.; Rossi, F.; Lampa, E.; Vacca, C.; Brita, G.; Saini, R.-K.; Di Nola, R. Agressologie 1976, 17, 279-295. Pedragosa-Moreau, S.; Morisseau, C.; Baratti, J.; Zylber, J.; Archelas, A.; Furstoss, R. Tetrahedron 1997, 53, 9707-9714.
10. (h) Unsubstituted: Mitchell, D.; Koenig, T. M. Synth. Commun. 1995, 25, 1231-1238. Coote, S. J.; Davies, S. G.; Middlemiss, D.; Naylor, A. S. J. Chem. Soc., Perkins Trans 1 1989, 2223-2228.
11. (h) Unsubstituted: Mitchell, D.; Koenig, T. M. Synth. Commun. 1995, 25, 1231-1238. Coote, S. J.; Davies, S. G.; Middlemiss, D.; Naylor, A. S. J. Chem. Soc., Perkins Trans 1 1989, 2223-2228.
12. (i) Various: Atkins, R. K.; Frazier, J.; Moore, L. L.; Weigel, L. O.; Tetrahedron Lett. 1986, 27, 2451-2454. Pfeiffer, F. R.; Wilson, J. W.; Weinstock, J.; Kuo, G. Y.; Chambers, P. A.; Holden, K. G.; Hahn, R. A.; Wardell, J. R.; Tobia, A. J.; Setler, P. E.; Sarau, H. M. J. Med. Chem. 1982, 25, 352-358.
13. (i) Various: Atkins, R. K.; Frazier, J.; Moore, L. L.; Weigel, L. O.; Tetrahedron Lett. 1986, 27, 2451-2454. Pfeiffer, F. R.; Wilson, J. W.; Weinstock, J.; Kuo, G. Y.; Chambers, P. A.; Holden, K. G.; Hahn, R. A.; Wardell, J. R.; Tobia, A. J.; Setler, P. E.; Sarau, H. M. J. Med. Chem. 1982, 25, 352-358.
14. (a) Arch, J. R. S.; Ainsworth, A. T.; Cawthorne, M. A.; Piercy, V.; Sennitt, M. V.; Thody, V. E.; Wilson, C.; Wilson, S. Nature 1984, 309, 163-165.
15. (b) Bloom, J. D.; Dutia, M. D.; Johnson, B. D.; Wissner, A.; Burns, M. G.; Largis, E. E.; Dolan, J. A.; Claus, T. H. J. Med. Chem. 1992, 35, 3081-3084.
16. (c) Badone, D.; Guzzi, U. Bioorg. Med. Chem. Lett. 1994, 4, 1921-1924.
17. (d) Cecchi, R.; Croci, T.; Boigegrain, R.; Boveri, S.; Baroni, M.; Boccardi, G.; Guimbard, J. P.; Guzzi, U. Eur. J. Med. Chem. 1994, 29, 259-267.
18. (e) Hattori, K.; Nagano, M.; Kato, T.; Nakanishi, I.; Imai, K.; Kinoshita, T.; Sakane, K. Bioorg. Med. Chem. Lett. 1995, 5, 2821-2824. General yields (81-95% yield) reported for several substrates which included 3-chlorostyrene oxide.
19. (f) Sher, P. M.; Fisher, L. G.; Skwish, S.; Michel, I. M.; Seiler, S. M.; Washburn, W. N.; Dickinson, K. E. J. Med. Chem. Res. 1997, 7, 109-115.
20. Matsuyama, A.; Kobayashi, Y. European Patent 0 611 826 A2, 1994.
21. (a) Xylene oxygenase two-liquid phase culture (96±2% ee, no yield), reaction with 3-chlorostyrene as 1% (v/v) of the organic phase; Wubbolts, M. G.; Hoven, J.; Melgert, B.; Witholt, B. Enzyme Microb. Technol. 1994, 16, 887-894.
22. (b) M(salen) and PhIO (46% ee, 60% Y); Ho, C.-W.; Cheng, W.-C.; Cheng, M.-C.; Peng, S.-M.; Cheng, K.-F. and Che, C.-M. J. Chem. Soc., Dalton Trans. 1996, 405-414.
23. (c) Ru(II) Schiff base complex and iodosylbenzene (72% ee, 48% conv.); Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R. J. Mol. Cat. A-Chem. 1995, 96, 117-122.
24. (d) Chloroperoxidase and t-BuOOH (62% ee (R), 34% Y); Colonna, S.; Gaggero, N.; Casella, L; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1993, 4, 1325-1330
25. (e) Co complexes and PhIO (up to 13% ee, 65% Y); Ozaki, S.; Mimura, H.; Yasuhara, N.; Masui, M.; Yamagata, Y.; Tomita, K.; Collins, T. J. J. Chem. Soc., Perkins Trans 2 1990, 353-360.
26. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
27. Pettman, R. B. Speciality Chemicals 1997, 118-120.
28. Two commercial suppliers of racemic 1 are listed in Chem Sources International (1996); however, both companies informed us that they did not maintain stocks of that material.
29. Jacobsen, E. N. In Comprehensive Organometallic Chemistry II, Wilkinson, G.; Stone, F. G. A.; Abel, E. W.; Hegedus, L. S. Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 11.1.
30. (a) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333-9334.
31. (b) Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457-5460.
32. A 23% NaCl solution freezes at -20.5°C. The Merck Index; Budavari, S. Ed.; Merck and Co. Inc.: Rahway, NJ USA 1996 no. 8742.
33. Racemic 1 provided epoxide in 99% ee and 45% yield, and diol in 90% ee and 44% yield; 36% ee 1 provided epoxide in 99% ee and 63% yield, and diol in 87% ee and 27% yield.
34. 20=+21 (neat).
35. (R,R) or (S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino- manganese(III) chloride. Literature synthesis: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939-1942. Larrow, J. F.; Jacobsen, E. N. Organic Synth., in press.
36. (R,R) or (S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino- manganese(III) chloride. Literature synthesis: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939-1942. Larrow, J. F.; Jacobsen, E. N. Organic Synth., in press.
37. Pospisil, P. J.; Carsten, D. H.; Jacobsen, E. N. Chem. Eur. J. 1996, 2, 974-980.
38. Procedure modified from (a) Ray, F. E.; Farmer, J. L. J. Org. Chem. 1943, 8, 391-396.
39. (b) Haridas, K.; Dev, S. Indian J. Chem. 1987, 26B, 1018-1020.
40. (c) Kaufman, T. Synthetic Commun. 1993, 23, 473-486.
41. (d) Merz, A.; Märkl, G. Angew. Chem., Int. Ed. Engl. 1973, 12, 845-846 (phase transfer conditions).
42. CAUTION!: very toxic cancer-suspect reagent. Use extreme caution in handling.
43. The reaction rate is dependent largely on the rate of stirring. More vigorous stirring leads to shorter reaction times and no deleterious effects on yield or enantioselectivity.
44. The amount of NaCl was not optimized, but was added simply to lower the melting point of the aqueous bleach phase and therefore allow the use of lower reaction temperatures.
45. 2O). Bortolini, O.; Campestrini, S.; DiFuria, F.; Modena, G. J. Org. Chem. 1987, 52, 5093-5095.
46. Boiling point of diol 189-191°C at 5 mmHg.
47. Hudlicky, T.; Boros, E. E.; Boros, C. H. Tetrahedron: Asymmetry 1993, 4, 1365-1368.