Asymmetric catalytic synthesis of α-aryloxy alcohols: Kinetic resolution of terminal epoxides via highly enantioselective ring-opening with phenols

Journal of the American Chemical Society

Volumn 121, Issue 25, 1999, Pages 6086-6087

  Ready, Joseph M ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; HYDROLYSIS; KINETICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0033618105     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9910917     Document Type: Article

References (22)

1. (a) Wright, J. L.; Gregory, T. F.; Heffner, T. G.; MacKenzie, R. G.; Pugsley, T. A.; Meulen, S. V.; Wise, L. D. Bioorg. Med. Chem. Lett. 1997, 7, 1377.
2. (b) Baker, N. R.; Byrne, N. G.; Economides, A. P.; Javeld, T. Chem. Pharm. Bull. 1995, 1045.
3. (c) Kirkup, M. P.; Rizvi, R.; Shankar, B. B.; Dugar, S.; Clader, J.; McCombie, S. W.; Lin, S.; Yumibe, N.; Huie, K.; Heek, M.; Compton, D. S.; Davis, H, R.; McPhail, A. T. Bioorg. Med. Chem. Lett. 1996, 6, 2069.
4. For examples of asymmetric reductions of α-arlyoxy ketones, see: (a) Takahashi, H.; Sakuraba, S.; Takea, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5877. (b) Gooding, O.; Colin, B.; Cooper, G.; Jackson, D. J. Org. Chem. 1993, 58, 3681. (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. (d) Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317. (e) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547.
5. For examples of asymmetric reductions of α-arlyoxy ketones, see: (a) Takahashi, H.; Sakuraba, S.; Takea, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5877. (b) Gooding, O.; Colin, B.; Cooper, G.; Jackson, D. J. Org. Chem. 1993, 58, 3681. (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. (d) Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317. (e) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547.
6. For examples of asymmetric reductions of α-arlyoxy ketones, see: (a) Takahashi, H.; Sakuraba, S.; Takea, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5877. (b) Gooding, O.; Colin, B.; Cooper, G.; Jackson, D. J. Org. Chem. 1993, 58, 3681. (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. (d) Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317. (e) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547.
7. For examples of asymmetric reductions of α-arlyoxy ketones, see: (a) Takahashi, H.; Sakuraba, S.; Takea, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5877. (b) Gooding, O.; Colin, B.; Cooper, G.; Jackson, D. J. Org. Chem. 1993, 58, 3681. (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. (d) Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317. (e) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547.
8. For examples of asymmetric reductions of α-arlyoxy ketones, see: (a) Takahashi, H.; Sakuraba, S.; Takea, H.; Achiwa, K. J. Am. Chem. Soc. 1990, 112, 5877. (b) Gooding, O.; Colin, B.; Cooper, G.; Jackson, D. J. Org. Chem. 1993, 58, 3681. (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. (d) Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317. (e) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547.
9. Shibasaki has reported the asymmetric catalytic ring opening of meso epoxides with 4-methoxyphenol using a Ga(BINOL) catalyst system: Lida, T.; Yamamoto, N.; Matsunaga, S.; Shigeki, M.; Woo, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223.
10. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen. E. N. Science 1997, 277, 936.
11. 2 open to the atmosphere for 45 min and then removing the solvent by rotary evaporation. See Supporting Information.
12. General procedure for the kinetic resolutions in Table 1 and Table 2: A 10 mL flask was charged with 86 mg (0.100 mmol) of 3c and 100 mg MS 3A. Epoxide (5.00 mmol) and phenol (2.25 mmol) were added at the indicated reaction temperature, and then TBME (0.15 mL) was added. The reaction was stirred at the indicated temperature until GC analysis indicated complete conversion of phenol, at which time 75 mg (0.30 mmol) pyridinium p-toluenesulfonate was added. The reaction mixture was filtered through a pad of silica and washed with 50% EtOAc/hexanes. The filtrate was concentrated and purified by chromatography on silica gel with EtOAc/hexanes or Kugelrohr distillation under reduced pressure. The enatiomeric purity was determined by GC or HPLC.
13. Full experimental procedures, spectral data for new compounds, and ee determinations are presented in the Supporting Information.
14. rel thus determined ranged from 42 (Table 2, entry 8) to greater than 300 (Table 1, entry 2, Table 2, entries 3, 4, 7, 9). Calculations for each entry are presented in the Supporting Information.
15. (a) Furrow, M. E.; Schaus, S.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776.
16. (b) Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937.
17. 3 has been reported, but we have no evidence for such a pathway in the present system. Takfichi, R.; Arihara, M.; Ishimori, M.; Tsuruta, T. Tetrahedron 1980, 36, 3391.
18. (a) Hansen, K.; Leighton, J.; Jacobsen, E. J. Am. Chem. Soc. 1996, 118, 10924.
19. (b) McCleland, B.; Nugent, W.; Finn, M. J. Org. Chem. 1998, 63, 6656.
20. + complex. (13) For related structures, see: (a) Cesari, M.; Neri, C.; Percgo, G.; Perrotti, E.; Zazzetta, A. J. Chem. Soc., Chem. Commun. 1970, 276. (b) Bailey, N. A.; McKenzie, E. D.; Worthington, J. M. J. Chem. Soc., Dalton Trans. 1977, 763. (c) Huilan, C.; Deyan, H.; Tian, L.; Hong, Y.; Wenxia, T.; Chen, J. Zheng, P.; Chen, C. Inorg. Chem. 1996, 35, 1502.
21. + complex. (13) For related structures, see: (a) Cesari, M.; Neri, C.; Percgo, G.; Perrotti, E.; Zazzetta, A. J. Chem. Soc., Chem. Commun. 1970, 276. (b) Bailey, N. A.; McKenzie, E. D.; Worthington, J. M. J. Chem. Soc., Dalton Trans. 1977, 763. (c) Huilan, C.; Deyan, H.; Tian, L.; Hong, Y.; Wenxia, T.; Chen, J. Zheng, P.; Chen, C. Inorg. Chem. 1996, 35, 1502.
22. + complex. (13) For related structures, see: (a) Cesari, M.; Neri, C.; Percgo, G.; Perrotti, E.; Zazzetta, A. J. Chem. Soc., Chem. Commun. 1970, 276. (b) Bailey, N. A.; McKenzie, E. D.; Worthington, J. M. J. Chem. Soc., Dalton Trans. 1977, 763. (c) Huilan, C.; Deyan, H.; Tian, L.; Hong, Y.; Wenxia, T.; Chen, J. Zheng, P.; Chen, C. Inorg. Chem. 1996, 35, 1502.