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Volumn 68, Issue 15, 2003, Pages 5983-5991

Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS;

EID: 0038711285     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342424     Document Type: Article
Times cited : (57)

References (50)
  • 2
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    • Paquette, L. A., Ed.; Wiley, New York
    • (b) Ciganek, E. Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201.
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    • Ciganek, E.1
  • 28
    • 0033992225 scopus 로고    scopus 로고
    • Li, G.; Wei, H. X.; Gao, J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1. In this paper Li and co-workers have clearly mentioned that the electron-withdrawing group is necessary on the aromatic ring for obtaining modest yields and a better reaction rate in the titanium tetrachloride mediated Baylis-Hillman reaction between aromatic aldehydes and cyclic enones and they employed 4-nitrobenzaldehyde and 4-(trifluoromethyl)benzaldehyde as electrophiles in this reaction.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1
    • Li, G.1    Wei, H.X.2    Gao, J.3    Caputo, T.D.4
  • 30
    • 0037595601 scopus 로고    scopus 로고
    • note
    • 3, (of the cyclohex-2-enone moiety) are on the same side in the extended conformation].
  • 31
    • 0038270821 scopus 로고    scopus 로고
    • note
    • Detailed X-ray crystallographic data for compound 5 is available from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, U.K. (CCDC no. 184079).
  • 32
    • 0038609708 scopus 로고    scopus 로고
    • note
    • 1H NMR data (particularly the chemical shifts of benzylic and/or olefinic protons) of Baylis-Hillman and aldol compounds obtained from cyclohex-2-enone and aromatic aldehydes were reported in the literature.
  • 33
    • 0038270818 scopus 로고    scopus 로고
    • note
    • 8
  • 34
    • 0038609709 scopus 로고    scopus 로고
    • note
    • 8,11 it may not be possible to confirm the complete absence of syn-aldol product because of the possibility of the doublet (or dd in case benzylic-H couples with the OH proton) hidden in this multiplet. Because the intensity of this multiplet itself (at δ 5.42-5.52) is much lower than that of singlet at δ 5.56, the syn-aldol product, even if formed, might be in much smaller amounts in comparison with that of the Baylis-Hillman adduct. These observations might, therefore, suggest that aldehydes undergo preferentially the Baylis-Hillman reaction.
  • 35
    • 0037029772 scopus 로고    scopus 로고
    • It is worth mentioning here the work of Zaidlewich and co-workers, who reported an interesting enolization-aldolization of cyclohex-2-enone derivatives via dienolborinates. During their studies they also observed the formation of Baylis-Hillman adducts in minor amounts in the case of dienolborinates derived from hindered cyclo-hexenones (3,4,5-trisubstituted cyclohexenone derivatives) along with major aldol adducts; see: Zaidlewicz, M.; Sokol, W.; Wojtczak, A.; Neumann, P.; Nissinen, M. Tetrahedron Lett. 2002, 43, 3525.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3525
    • Zaidlewicz, M.1    Sokol, W.2    Wojtczak, A.3    Neumann, P.4    Nissinen, M.5
  • 36
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    • 12a,b (a) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (b) Shi, M.; Jiang, J.-K.; Cui, S.-C. Tetrahedron 2001, 57, 7343. (c) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
    • (2001) J. Org. Chem. , vol.66 , pp. 406
    • Shi, M.1    Feng, Y.-S.2
  • 37
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    • 12a,b (a) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (b) Shi, M.; Jiang, J.-K.; Cui, S.-C. Tetrahedron 2001, 57, 7343. (c) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
    • (2001) Tetrahedron , vol.57 , pp. 7343
    • Shi, M.1    Jiang, J.-K.2    Cui, S.-C.3
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    • 12a,b (a) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406. (b) Shi, M.; Jiang, J.-K.; Cui, S.-C. Tetrahedron 2001, 57, 7343. (c) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
    • (2000) Org. Lett. , vol.2 , pp. 2397
    • Shi, M.1    Jiang, J.-K.2    Feng, Y.-S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.