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Volumn 44, Issue 50, 2003, Pages 8975-8977

The first C2 selective halide substitution reaction of 2,3-epoxy alcohols by the use of (CH3O)3B-MX (X=I, Br, Cl) system

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALCOHOL DERIVATIVE; BORON DERIVATIVE; BROMINE; CHLORINE; HALIDE; IODINE; SODIUM IODIDE;

EID: 0242541976     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.001     Document Type: Article
Times cited : (24)

References (25)
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    • For C2 selective reactions with carbon nucleophiles, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (c) Chong, J. M.; Cyr, D. R. ; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012; (d) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631; (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765-1767.
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    • Johnson, M.R.1    Nakata, T.2    Kishi, Y.3
  • 6
    • 33845550538 scopus 로고
    • For C2 selective reactions with carbon nucleophiles, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (c) Chong, J. M.; Cyr, D. R. ; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012; (d) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631; (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765-1767.
    • (1983) J. Org. Chem. , vol.48 , pp. 4131-4132
    • Tius, M.A.1    Fauq, A.H.2
  • 7
    • 0000395222 scopus 로고
    • For C2 selective reactions with carbon nucleophiles, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (c) Chong, J. M.; Cyr, D. R. ; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012; (d) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631; (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765-1767.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5009-5012
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  • 8
    • 0001083151 scopus 로고
    • For C2 selective reactions with carbon nucleophiles, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (c) Chong, J. M.; Cyr, D. R. ; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012; (d) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631; (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765-1767.
    • (1992) Org. React. , vol.41 , pp. 135-631
    • Lipshutz, B.H.1    Sengupta, S.2
  • 9
    • 0012555742 scopus 로고    scopus 로고
    • For C2 selective reactions with carbon nucleophiles, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (c) Chong, J. M.; Cyr, D. R. ; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012; (d) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631; (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765-1767.
    • (2001) Org. Lett. , vol.3 , pp. 1765-1767
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    • Bonini C., Giuliano C., Righi G., Sotgiu G. J. Org. Chem. 56:1991;6206-6209 Bovicelli, P.; Lupattelli, M.; Bersani, M. T.; Mincione, E. Tetrahedron Lett. 1992, 33, 6181-6182. See also Ref. 6.
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    • Bonini, C.1    Giuliano, C.2    Righi, G.3    Sotgiu, G.4
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    • note
    • 4 resulted in selective cleavage of 1,2-diol 3, and the stereochemistry of 1,3-diol 2 was confirmed after conversion into the corresponding acetonide derivative.


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