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Volumn 64, Issue 18, 1999, Pages 6815-6821

A mechanistic study of the Horner-Wadsworth-Emmons reaction: Computational investigation on the reaction pass and the stereochemistry in the reaction of lithium enolate derived from trimethyl phosphonoacetate with acetaldehyde

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; LITHIUM DERIVATIVE; PHOSPHONOACETIC ACID;

EID: 0032887595     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909150     Document Type: Article
Times cited : (87)

References (48)
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    • For reviews of the Horner-Wadsworth-Emmons reaction, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
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    • (b) Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
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    • (c) Ando, K. J. Org. Chem. 1998, 63, 8411-8416.
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    • Ando, K.1
  • 21
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    • Also see ref 1a
    • (a) For a leading mechanistic review, see; Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1. Also see ref 1a.
    • (1994) Top. Stereochem. , vol.21 , pp. 1
    • Vedejs, E.1    Peterson, M.J.2
  • 22
    • 0032486777 scopus 로고    scopus 로고
    • and references therein
    • (b) Yamataka, H.; Nagase, S. J. Am. Chem. Soc. 1998, 120, 7530-7536 and references therein.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7530-7536
    • Yamataka, H.1    Nagase, S.2
  • 31
    • 85021596191 scopus 로고
    • 8a However, we believe that the system containing countercation is very important. Even tertrabutylammonium enolates derived from malonates have a U-shaped structure, just like metal enolates of 1,3-dicarbonyl compounds: Reetz, M. T.; Hütte, S.; Goddard, R. J. Am. Chem. Soc. 1993, 115, 9339-9340.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9339-9340
    • Reetz, M.T.1    Hütte, S.2    Goddard, R.3
  • 34
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    • note
    • Diffuse functions allow orbitals to occupy a larger region of space. Basis sets with diffuse functions are important for systems where electrons are relatively far from the nucleus: anions, molecules with lone pairs, and so on.
  • 36
    • 0345491105 scopus 로고
    • (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. For reviews of density-functional methods see:
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 45
    • 0001474766 scopus 로고
    • Although the lithium enolates exist as aggregates in solution, a monomeric species is the reactive intermediate at least in some cases: Abbotto, A.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 6358-6359.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6358-6359
    • Abbotto, A.1    Streitwieser, A.2
  • 46
    • 0001624349 scopus 로고
    • Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737-2769. Luch, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009-6010. Hitchcock, P. B.; Lappert, M. F.; Layh, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 501-504.
    • (1977) Tetrahedron , vol.33 , pp. 2737-2769
    • Jackman, L.M.1    Lange, B.C.2
  • 47
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    • Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737-2769. Luch, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009-6010. Hitchcock, P. B.; Lappert, M. F.; Layh, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 501-504.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6009-6010
    • Luch, B.L.1    Collum, D.B.2
  • 48
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    • Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737-2769. Luch, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009-6010. Hitchcock, P. B.; Lappert, M. F.; Layh, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 501-504.
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    • Hitchcock, P.B.1    Lappert, M.F.2    Layh, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.