Stereoselective reductive rearrangement of α-hydroxy epoxides: A new method for synthesis of 1,3-diols

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 629-633

  Tu, Yong Qiang ^a   Sun, Liang Dong ^a   Wang, Ping Zhen ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0001647186     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981097z     Document Type: Article

References (25)

1. This work has been registered as a Chinese Patent, 97118857.2, 1997.
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4. For Lewis acid-catalyzed rearrangements of epoxides, see: (a) for general review, Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, pp 733-755. (b)-Morgans, D. J.; Sharpless K. B. J. Am. Chem. Soc. 1981, 103, 462-464. (c) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. J. Am. Chem. Soc. 1986, 108, 3827- 3830. (d) Maruoka, K.; Sato, J.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5449-5450. (e) Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944- 5951.
5. For Lewis acid-catalyzed rearrangements of epoxides, see: (a) for general review, Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, pp 733-755. (b)- Morgans, D. J.; Sharpless K. B. J. Am. Chem. Soc. 1981, 103, 462- 464. (c) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. J. Am. Chem. Soc. 1986, 108, 3827-3830. (d) Maruoka, K.; Sato, J.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5449-5450. (e) Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944- 5951.
6. For Lewis acid-catalyzed rearrangements of epoxides, see: (a) for general review, Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, pp 733-755. (b)- Morgans, D. J.; Sharpless K. B. J. Am. Chem. Soc. 1981, 103, 462- 464. (c) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. J. Am. Chem. Soc. 1986, 108, 3827- 3830. (d) Maruoka, K.; Sato, J.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5449-5450. (e) Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944- 5951.
7. For Lewis acid-catalyzed rearrangements of epoxides, see: (a) for general review, Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, pp 733-755. (b)- Morgans, D. J.; Sharpless K. B. J. Am. Chem. Soc. 1981, 103, 462- 464. (c) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. J. Am. Chem. Soc. 1986, 108, 3827- 3830. (d) Maruoka, K.; Sato, J.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5449-5450. (e) Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944-5951.
8. For some synthetic applications of epoxides, see: (a) Gorzynski Smith, J. Synthesis 1984, 8, 629-656. (b) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (c) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D.; Ed.; Academic Press: Orlando, FL, 1983; Vol. 5, pp 194-246.
9. For some synthetic applications of epoxides, see: (a) Gorzynski Smith, J. Synthesis 1984, 8, 629-656. (b) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (c) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D.; Ed.; Academic Press: Orlando, FL, 1983; Vol. 5, pp 194-246.
10. For some synthetic applications of epoxides, see: (a) Gorzynski Smith, J. Synthesis 1984, 8, 629-656. (b) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367. (c) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D.; Ed.; Academic Press: Orlando, FL, 1983; Vol. 5, pp 194-246.
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16. For synthesis of chiral spirocyclic diols and their application to asymmetric organic reaction, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.- C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570-9571. (b) Chan, A. S. C.; Lin, C.-C.; Sun, J.; Hu, W.; Li, Z.; Pan, W.; Mi, A.; Jiang, Y.; Huang, T.-M.; Yang, T.-K.; Chen, J.-H.; Wang, Y.; Lee, G.-H. Tetrahedron: Asymmetry 1995, 6, 2953-2959. (c) Brünner, R.; Gerlach, H. Tetrahedron: Asymmetry 1994, 5, 1613-1620. (d) Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (e) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973-1976. (f) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans. 1 1977, 2411-2416.
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18. For synthesis of chiral spirocyclic diols and their application to asymmetric organic reaction, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.- C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570-9571. (b) Chan, A. S. C.; Lin, C.-C.; Sun, J.; Hu, W.; Li, Z.; Pan, W.; Mi, A.; Jiang, Y.; Huang, T.-M.; Yang, T.-K.; Chen, J.-H.; Wang, Y.; Lee, G.-H. Tetrahedron: Asymmetry 1995, 6, 2953-2959. (c) Brünner, R.; Gerlach, H. Tetrahedron: Asymmetry 1994, 5, 1613-1620. (d) Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (e) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973-1976. (f) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans. 1 1977, 2411-2416.
19. For synthesis of chiral spirocyclic diols and their application to asymmetric organic reaction, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.- C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570-9571. (b) Chan, A. S. C.; Lin, C.-C.; Sun, J.; Hu, W.; Li, Z.; Pan, W.; Mi, A.; Jiang, Y.; Huang, T.-M.; Yang, T.-K.; Chen, J.-H.; Wang, Y.; Lee, G.-H. Tetrahedron: Asymmetry 1995, 6, 2953-2959. (c) Brünner, R.; Gerlach, H. Tetrahedron: Asymmetry 1994, 5, 1613-1620. (d) Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (e) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973-1976. (f) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans. 1 1977, 2411-2416.
20. For synthesis of chiral spirocyclic diols and their application to asymmetric organic reaction, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.- C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570-9571. (b) Chan, A. S. C.; Lin, C.-C.; Sun, J.; Hu, W.; Li, Z.; Pan, W.; Mi, A.; Jiang, Y.; Huang, T.-M.; Yang, T.-K.; Chen, J.-H.; Wang, Y.; Lee, G.-H. Tetrahedron: Asymmetry 1995, 6, 2953-2959. (c) Brünner, R.; Gerlach, H. Tetrahedron: Asymmetry 1994, 5, 1613-1620. (d) Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. J. Chem. Soc., Perkin Trans. 1 1994, 3441-3447. (e) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973-1976. (f) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans. 1 1977, 2411-2416.
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23. 3, affording only a complicated mixture.
24. In some examples, a larger scale of experiment (e.g., with > 1 g of 12a) gave a little lower stereoslectivity of the C-1 center (ca. 5% of 1-epimer of 12b was formed).
25. 1-aromactic substituted substrates generally gave products with lower selectivity of C-1 though the reaction yield was generally high.