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Volumn 37, Issue 23, 1996, Pages 3955-3958

A convenient synthesis of protected and free homoallylic alcohols: Catalytic use of dibutyltin dichloride in the allylation of aldehydes with allyltributyltin

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

EID: 0029927159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00719-8     Document Type: Article
Times cited : (11)

References (26)
  • 1
    • 4243893500 scopus 로고
    • For reviews of allylmetal additions to carbonyl compounds, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 2
    • 0002446724 scopus 로고
    • Trost, B.M., Ed.; Pergamon Press: Oxford
    • (b) Roush, W.R. In Comprehensive Organic Synthesis, Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 3
    • 0002313620 scopus 로고    scopus 로고
    • For reviews of the addition of allylic tin reagents to carbonyl compounds, see: (a) Marshall, J.A. Chem. Rev. 1996, 96, 31.
    • (1996) Chem. Rev. , vol.96 , pp. 31
    • Marshall, J.A.1
  • 10
    • 0027501692 scopus 로고
    • For a highly effective catalytic enantioselective allylation based on a titanium/BINOL complex, see: (a) Keck, G.E.; Geraci, L.S. Tetrahedron Lett. 1993, 34, 7827.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7827
    • Keck, G.E.1    Geraci, L.S.2
  • 16
    • 0343826519 scopus 로고
    • Paquette, L.A., Ed.; John Wiley and Sons: Chichester
    • For a review of the preparation and reactions of allyldibutyltin chloride, see: Tagliavini, G. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; John Wiley and Sons: Chichester, 1995; Vol. 1, p 98.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.1 , pp. 98
    • Tagliavini, G.1
  • 22
    • 85030205334 scopus 로고    scopus 로고
    • note
    • 2) or elution through a short plug of Florisil® with Skelly B (silyl ethers) afforded the pure alcohol derivatives as colorless oils.
  • 23
    • 85030206294 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy of the crude reaction mixture. The exchange reaction in eq 5 may not be favorable under these conditions.
  • 24
    • 85030205930 scopus 로고    scopus 로고
    • note
    • (formula presented)
  • 25
    • 85030210341 scopus 로고    scopus 로고
    • note
    • The following electrophiles provided no protected product in the case of benzaldehyde: methyl iodide; methanesulfonyl chloride; and t-butyldimethylsilyl chloride. Chloromethyl methyl ether gave complex mixures in the presence and absence of catalyst. The use of trimethylsilyl chloride with cinnamaldehyde and cyclohexanecarboxaldehyde gave product mixtures.
  • 26
    • 85030205621 scopus 로고    scopus 로고
    • note
    • 4. Evaporation of solvent (residual water was usually present, but no attempt was made to remove it) followed by chromatography of the residue (5:1 Skelly B / EtOAc) yielded the alcohol products as colorless oils.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.