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Volumn 15, Issue 23, 2004, Pages 3653-3691

Enantioselective protonations: Fundamental insights and new concepts

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACID; ALCOHOL DERIVATIVE; AMINE; ETHER DERIVATIVE; KETENE DERIVATIVE; PROTON;

EID: 9644291545     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.09.035     Document Type: Review
Times cited : (150)

References (190)
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    • Launay, J. C. Ph. D. Thesis, Rouen, 1986
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    • P. Duhamel J.R. Desmurs S. Ratton The Roots of Organic Chemistry 1995 Elsevier Amsterdam 177 188
    • (1995) The Roots of Organic Chemistry , pp. 177-188
    • Duhamel, P.1
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    • unpublished results
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    • Duhamel, L.1
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    • C. Fehr Chimia 45 1991 253 261
    • (1991) Chimia , vol.45 , pp. 253-261
    • Fehr, C.1
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    • G. Helmchen R.W. Hoffmann J. Mulzer E. Schaumann G. Thieme Stuttgart
    • S. Hünig G. Helmchen R.W. Hoffmann J. Mulzer E. Schaumann Houben-Weyl: Methods of Organic Chemistry Vol. E 21d 1995 G. Thieme Stuttgart 3851 3999
    • (1995) Houben-Weyl: Methods of Organic Chemistry , vol.21 , pp. 3851-3999
    • Hünig, S.1
  • 120
    • 9644312401 scopus 로고
    • Some examples of thermodynamically controlled deracemizations: H. Stecher, and K. Faber Synthesis 1987 1 16
    • (1987) Synthesis , pp. 1-16
    • Stecher, H.1    Faber, K.2
  • 124
    • 0035802951 scopus 로고    scopus 로고
    • For recent discussion about deracemization concept, see: K. Faber Chem. Eur. J. 7 2001 5004 5010
    • (2001) Chem. Eur. J. , vol.7 , pp. 5004-5010
    • Faber, K.1
  • 142
    • 9644297523 scopus 로고    scopus 로고
    • note
    • 9g
  • 143
    • 9644310890 scopus 로고    scopus 로고
    • note
    • 9a
  • 144
    • 9644298692 scopus 로고
    • 1g,1i Another interpretation may be the variation of the crowding of the aromatic nucleus with the electronic effects of the substituents J.P. Guetté, M. Perlat, J. Capillon, and D. Boucherot Tetrahedron Lett. 1974 2409 2410
    • (1974) Tetrahedron Lett. , pp. 2409-2410
    • Guetté, J.P.1    Perlat, M.2    Capillon, J.3    Boucherot, D.4
  • 147
    • 9644293562 scopus 로고    scopus 로고
    • note
    • In the case of palladium enolates, the chirality is carried by the ligands of palladium [(R)-BINAP]. The chiral palladium enolate, catalytically generated from a trimethylsilyl enolether is protonated by an achiral agent, water
  • 169
    • 9644298266 scopus 로고    scopus 로고
    • note
    • (b) For the four models shown in Schemes 12 and 13, the attack by H-A* can occur on the same face of the paper, either above as depicted in Schemes 12 and 13 or behind. Obviously, the attack can also occur above (or behind) for the E- and Z-models of the RSC reaction (Scheme 12) and behind (or above) for the E- and Z-models of the NSC reaction (Schemes 13)
  • 170
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    • An example of this reaction type is reported in the hydrogenation of methyl 3-acetamido-2-butenoate by the Ru-BINAP system: the Z-isomer gave 96% ee while the E-isomer gave only 5% ee with an opposite configuration: W.D. Lubell, M. Kitamura, and R. Noyori Tetrahedron: Asymmetry 2 1991 543 554
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 543-554
    • Lubell, W.D.1    Kitamura, M.2    Noyori, R.3
  • 172
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    • note
    • 7w,7y
  • 173
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    • note
    • 10f
  • 186
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    • note
    • 2e,2g
  • 187
    • 9644299042 scopus 로고    scopus 로고
    • note
    • This type of reaction is sometimes considered as a diastereoselective protonation


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.