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Volumn 68, Issue 4, 2003, Pages 1585-1588

Transformation of α,β-epoxyesters into 2,3-dideuterioesters promoted by samarium diiodide

Author keywords

[No Author keywords available]

Indexed keywords

SATURATED ESTERS;

EID: 0037458996     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026043a     Document Type: Article
Times cited : (19)

References (26)
  • 1
    • 0000473902 scopus 로고
    • For a review on epoxide chemistry and reactivity, see: (a) Rao, A. S.; Panikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2365. (b) Gorzynski-Smith, J. Synthesis 1984, 629-656. (c) For some recent synthetic application of epoxides, see: Taylor, S. K. Tetrahedron 2000, 56, 1149-1163. (d) Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 63, 2164-2165.
    • (1983) Tetrahedron , vol.39 , pp. 2323-2365
    • Rao, A.S.1    Panikar, S.K.2    Kirtane, J.G.3
  • 2
    • 85037455306 scopus 로고
    • For a review on epoxide chemistry and reactivity, see: (a) Rao, A. S.; Panikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2365. (b) Gorzynski-Smith, J. Synthesis 1984, 629-656. (c) For some recent synthetic application of epoxides, see: Taylor, S. K. Tetrahedron 2000, 56, 1149-1163. (d) Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 63, 2164-2165.
    • (1984) Synthesis , pp. 629-656
    • Gorzynski-Smith, J.1
  • 3
    • 0034712223 scopus 로고    scopus 로고
    • For a review on epoxide chemistry and reactivity, see: (a) Rao, A. S.; Panikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2365. (b) Gorzynski-Smith, J. Synthesis 1984, 629-656. (c) For some recent synthetic application of epoxides, see: Taylor, S. K. Tetrahedron 2000, 56, 1149-1163. (d) Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 63, 2164-2165.
    • (2000) Tetrahedron , vol.56 , pp. 1149-1163
    • Taylor, S.K.1
  • 4
    • 0033515487 scopus 로고    scopus 로고
    • For a review on epoxide chemistry and reactivity, see: (a) Rao, A. S.; Panikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2365. (b) Gorzynski-Smith, J. Synthesis 1984, 629-656. (c) For some recent synthetic application of epoxides, see: Taylor, S. K. Tetrahedron 2000, 56, 1149-1163. (d) Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 63, 2164-2165.
    • (1999) J. Org. Chem. , vol.63 , pp. 2164-2165
    • Hinterding, K.1    Jacobsen, E.N.2
  • 7
    • 0000180963 scopus 로고    scopus 로고
    • Transformation of 2,3-epoxy-3-phenylpropionic acid ethyl ester into 3-phenylpropionic acid ethyl ester by using a borohydride exchange resin has been described: Sim, T. B.; Yoon, N. M. Bull. Chem. Soc. Jpn. 1997, 70, 1101-1107.
    • (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 1101-1107
    • Sim, T.B.1    Yoon, N.M.2
  • 8
    • 0004253353 scopus 로고
    • Oxford University Press: Oxford
    • Mann, J. Secondary Metabolism; Oxford University Press: Oxford, 1986; p 23.
    • (1986) Secondary Metabolism , pp. 23
    • Mann, J.1
  • 10
    • 0033549735 scopus 로고    scopus 로고
    • (a) Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. Angew. Chem. 1999, 111, 2528-2530; Angew. Chem., Int. Ed. 1999, 38, 2384-2386.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2384-2386
  • 12
    • 0040184024 scopus 로고    scopus 로고
    • (b) Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem. 2000, 112, 2866-2868; Angew. Chem., Int. Ed. 2000, 39, 2773-2775.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2773-2775
  • 17
    • 2142715741 scopus 로고    scopus 로고
    • For recent reviews on sequenced reactions promoted by samarium diiodide: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (b) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354.
    • (1996) Chem. Rev. , vol.96 , pp. 307-338
    • Molander, G.A.1    Harris, C.R.2
  • 18
    • 0032473838 scopus 로고    scopus 로고
    • For recent reviews on sequenced reactions promoted by samarium diiodide: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (b) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354.
    • (1998) Tetrahedron , vol.54 , pp. 3321-3354
    • Molander, G.A.1    Harris, C.R.2
  • 19
    • 0000784042 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Rosen, T. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2; p 409.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 409
    • Rosen, T.1
  • 20
    • 0242582119 scopus 로고    scopus 로고
    • note
    • Compounds 1f and 1h were obtained from the corresponding α-bromoesters.
  • 22
    • 0242414393 scopus 로고    scopus 로고
    • note
    • + of the corresponding nondeuterated compound, indicating a presence of the nondeuterated compound <1%.
  • 23
    • 0000272655 scopus 로고
    • 2 in the presence of HMPA and N,N-dimethylaminoethanol, has been previously described: Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437-4440.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4437-4440
    • Otsubo, K.1    Inanaga, J.2    Yamaguchi, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.