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Volumn 46, Issue 38, 2005, Pages 6465-6468

Stereoselective acid-catalyzed homoallylic rearrangement of cyclopropylsilylmethanols: An efficient route to Z-homoallyl derivatives

Author keywords

Acylsilanes; Cyclopropylmethanol; Homoallylic rearrangement; Nucleophilic addition; Protiodesilylation

Indexed keywords

CARBON; CYCLOPROPANE DERIVATIVE; METHANOL DERIVATIVE;

EID: 23844492156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.092     Document Type: Article
Times cited : (25)

References (45)
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  • 25
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    • For reports about diastereoselective addition of nucleophiles to cyclopropyl ketones, see: S. Ono, S. Shuto, and A. Matsuda Tetrahedron Lett. 37 1996 221 224
    • (1996) Tetrahedron Lett. , vol.37 , pp. 221-224
    • Ono, S.1    Shuto, S.2    Matsuda, A.3
  • 28
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    • The nucleophilic addition to cyclopropyl silyl ketones and following 1,2-Brook rearrangement were reported, see: J. Clayden, D.W. Watson, and M. Chambers Tetrahedron 61 2005 3195 3203 Treatment of cyclopropyl silyl ketones with alkyllithium or phenyllithium, however, provided no Brook rearrangement products at all in our case
    • (2005) Tetrahedron , vol.61 , pp. 3195-3203
    • Clayden, J.1    Watson, D.W.2    Chambers, M.3
  • 29
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    • For reports about Julia ring opening of a cyclopropylmethanol, see: M.A. Brimble, and H. Prabaharan Tetrahedron 54 1998 2113 2128
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    • Brimble, M.A.1    Prabaharan, H.2
  • 34
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    • For metal-catalyzed transformation of cyclopropylmethanol into homoallylic derivatives, see: Y. Maeda, T. Nishimura, and S. Uemura Chem. Lett. 34 2005 380 381
    • (2005) Chem. Lett. , vol.34 , pp. 380-381
    • Maeda, Y.1    Nishimura, T.2    Uemura, S.3
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    • note
    • The dimethylphenylsilyl-substituted cyclopropylmethanols were exclusively used for the present study. The homoallylic rearrangement of trimethylsilyl-substituted homologue proceeded similarly, however lower reactivity was observed in the following protiodesilylation of the resulting trimethylsilyl-substituted homoallylic derivatives.
  • 43
    • 0000708435 scopus 로고
    • For leading references on the bisected conformation of cyclopropylcarbinyl cations, see: J. Haywood-Farmer Chem. Rev. 74 1974 315 350
    • (1974) Chem. Rev. , vol.74 , pp. 315-350
    • Haywood-Farmer, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.