A facile conversion of epoxides to β-halohydrins with silica gel-supported lithium halides

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1845-1848

  Kotsuki, Hiyoshizo ^a   Shimanouchi, Tomoyasu ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; CYCLOHEXANOL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; ORGANOBROMINE DERIVATIVE; ORGANOCHLORINE DERIVATIVE; ORGANOIODINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029921901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00159-1     Document Type: Article

References (24)

1. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley, 1972; Vol. 2, p 1; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323; Smith, J. G. Synthesis 1984, 629.
2. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley, 1972; Vol. 2, p 1; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323; Smith, J. G. Synthesis 1984, 629.
3. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley, 1972; Vol. 2, p 1; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323; Smith, J. G. Synthesis 1984, 629.
4. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley, 1972; Vol. 2, p 1; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323; Smith, J. G. Synthesis 1984, 629.
5. Sharpless, K. B. Chem. Brit. 1986, 22, 38; Pfenninger, A. Synthesis 1986, 89; Hanson, R. M. Chem. Rev. 1991, 91, 437.
6. Sharpless, K. B. Chem. Brit. 1986, 22, 38; Pfenninger, A. Synthesis 1986, 89; Hanson, R. M. Chem. Rev. 1991, 91, 437.
7. Sharpless, K. B. Chem. Brit. 1986, 22, 38; Pfenninger, A. Synthesis 1986, 89; Hanson, R. M. Chem. Rev. 1991, 91, 437.
8. Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159; Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. in press. See also: Raubo, P.; Wicha, J. Synlett 1993, 25; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703.
9. Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159; Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. in press. See also: Raubo, P.; Wicha, J. Synlett 1993, 25; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703.
10. Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159; Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. in press. See also: Raubo, P.; Wicha, J. Synlett 1993, 25; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703.
11. Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159; Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. in press. See also: Raubo, P.; Wicha, J. Synlett 1993, 25; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703.
12. For general reviews in this area, see: McKillop, A.; Young, D. W. Synthesis 1979, 401, 481; Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents: Preparation, Analysis, and Application, VCH, New York, 1992; Solid Supports and Catalysts in Organic Synthesis, Smith, K., Ed.; Ellis Horwood, New York, 1992.
13. For general reviews in this area, see: McKillop, A.; Young, D. W. Synthesis 1979, 401, 481; Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents: Preparation, Analysis, and Application, VCH, New York, 1992; Solid Supports and Catalysts in Organic Synthesis, Smith, K., Ed.; Ellis Horwood, New York, 1992.
14. For general reviews in this area, see: McKillop, A.; Young, D. W. Synthesis 1979, 401, 481; Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents: Preparation, Analysis, and Application, VCH, New York, 1992; Solid Supports and Catalysts in Organic Synthesis, Smith, K., Ed.; Ellis Horwood, New York, 1992.
15. Review: Bonini, C.; Righi, G. Synthesis 1994, 225.
16. Wakogel C-300 was employed throughout this work.
17. Satisfactory spectral and analytical data were obtained.
18. Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
19. Although the absolute configuration of these products was undetermined, the retention time for each enantiomer was 38.8 min and 43.9 min, respectively, as determined by HPLC analysis (254 nm) using a Chiralcel OJ column with 10% i-PrOH in hexane as eluant at a flow rate of 0.5 mL/min.
20. 3)].
21. Imuta, M.; Kawai, K.; Ziffer, H. J. Org. Chem. 1980, 45, 3352.
22. For a similar finding, see: Mandal, A. K.; Mahajan, S. W. Tetrahedron 1988, 44, 2293.
23. Larock, R. C. Comprehensive Organic Transformations, VCH, New York, 1989; pp 460-461.
24. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917 and references cited therein.