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Volumn 61, Issue 21, 1996, Pages 7455-7462

Diastereoselectivity in the Mukaiyama - Michael reaction employing α-acyl β,γ-unsaturated phosphonates

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EID: 0001230975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9510853     Document Type: Article
Times cited : (61)

References (61)
  • 23
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    • Diethyl (E)-but-2-enoylphosphonate [diethyl crotonylphosphonate; DECP, 1] was prepared by a Michaelis-Arbusov reaction between (E)-but-2-enoyl chloride and triethyl phosphite: See Szpala, A.; Tebby, J.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1 1981, 1363-66.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 1363-1366
    • Szpala, A.1    Tebby, J.2    Griffiths, D.V.3
  • 24
    • 85033826522 scopus 로고    scopus 로고
    • note
    • 4.
  • 25
    • 85033821499 scopus 로고    scopus 로고
    • note
    • Controlled experiments revealed that (E)-2 rapidly isomerizes to (Z)-2 under the reaction conditions.
  • 26
    • 0001218374 scopus 로고
    • Using the X-ray data for complex 7 as a rough structural analog, we believe that it is reasonable to propose that stannacycle 6 is monomeric in DECP and chelated to hexacoordinate tin as a cis complex. See Reetz, M. T.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 5881-84.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5881-5884
    • Reetz, M.T.1    Harms, K.2    Reif, W.3
  • 33
    • 37049061598 scopus 로고
    • 4·2L complexes have been previously discussed. However, the interplay between electronic and steric influences and the role these factors play in determining stability remain vague. See, (a) Smith, J. A. S.; Wilkins, E. J. Chem. Commun. 1965, 381. (b) Wilkins, C. J.; Haendler, H. M. J. Chem. Soc. 1965, 3174. (c) Hill, J. C.; Drago, R. S.; Herber, R. H. J. Am. Chem. Soc. 1969, 91, 1644. (d) Zahrobsky, R. F. J. Am. Chem. Soc. 1971, 93, 3313.
    • (1965) Chem. Commun. , pp. 381
    • Smith, J.A.S.1    Wilkins, E.J.2
  • 34
    • 37049044254 scopus 로고
    • 4·2L complexes have been previously discussed. However, the interplay between electronic and steric influences and the role these factors play in determining stability remain vague. See, (a) Smith, J. A. S.; Wilkins, E. J. Chem. Commun. 1965, 381. (b) Wilkins, C. J.; Haendler, H. M. J. Chem. Soc. 1965, 3174. (c) Hill, J. C.; Drago, R. S.; Herber, R. H. J. Am. Chem. Soc. 1969, 91, 1644. (d) Zahrobsky, R. F. J. Am. Chem. Soc. 1971, 93, 3313.
    • (1965) J. Chem. Soc. , pp. 3174
    • Wilkins, C.J.1    Haendler, H.M.2
  • 35
    • 3643106557 scopus 로고
    • 4·2L complexes have been previously discussed. However, the interplay between electronic and steric influences and the role these factors play in determining stability remain vague. See, (a) Smith, J. A. S.; Wilkins, E. J. Chem. Commun. 1965, 381. (b) Wilkins, C. J.; Haendler, H. M. J. Chem. Soc. 1965, 3174. (c) Hill, J. C.; Drago, R. S.; Herber, R. H. J. Am. Chem. Soc. 1969, 91, 1644. (d) Zahrobsky, R. F. J. Am. Chem. Soc. 1971, 93, 3313.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1644
    • Hill, J.C.1    Drago, R.S.2    Herber, R.H.3
  • 36
    • 0009133065 scopus 로고
    • 4·2L complexes have been previously discussed. However, the interplay between electronic and steric influences and the role these factors play in determining stability remain vague. See, (a) Smith, J. A. S.; Wilkins, E. J. Chem. Commun. 1965, 381. (b) Wilkins, C. J.; Haendler, H. M. J. Chem. Soc. 1965, 3174. (c) Hill, J. C.; Drago, R. S.; Herber, R. H. J. Am. Chem. Soc. 1969, 91, 1644. (d) Zahrobsky, R. F. J. Am. Chem. Soc. 1971, 93, 3313.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 3313
    • Zahrobsky, R.F.1
  • 59
    • 85033812110 scopus 로고
    • Unpublished results, The University of North Carolina at Chapel Hill
    • Poon, C.-D. Unpublished results, The University of North Carolina at Chapel Hill, 1995.
    • (1995)
    • Poon, C.-D.1
  • 61
    • 85033831985 scopus 로고    scopus 로고
    • note
    • The low yield in this reaction results from a competing dimerization reaction. See reference 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.