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Volumn 43, Issue 17, 2004, Pages 2280-2282

A novel 1,2-migration of acyloxy, phosphatyloxy, and sulfonyloxy groups in allenes: Efficient synthesis of tri- and tetrasubstituted furans

Author keywords

Cyclization; Furans; Homogeneous catalysis; Rearrangement; Synthetic methods

Indexed keywords

ISOMERIZATION; ISOMERS; POLYCYCLIC AROMATIC HYDROCARBONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

EID: 4544333104     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353535     Document Type: Article
Times cited : (186)

References (44)
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    • d) R. Mahrwald, H. Schick, Angew. Chem. 1991, 103, 577; Angew. Chem. Int. Ed. Engl. 1991, 30, 593;
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 593
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    • c) J. T. Kim, A. V. Kel'in, V. Gevorgyan, Angew. Chem. 2003, 115, 102; Angew. Chem. Int. Ed. 2003, 42, 98;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 98
  • 31
    • 4544358719 scopus 로고    scopus 로고
    • note
    • For 1,2-migration of the thio group proceeding through a thiirenium intermediate, see ref. [5c].
  • 32
    • 4544267404 scopus 로고    scopus 로고
    • note
    • 4 may participate in either or all steps of the sequence, as silver salts are known to catalyze propargylacyloxy [3,3]-sigmatropic shifts (see ref. [1]) as well as the cycloisomerization of allenyl ketones into furans.[11b,c]
  • 33
    • 4544388485 scopus 로고    scopus 로고
    • note
    • 4 in catalyzing this transformation.
  • 34
    • 4544350524 scopus 로고    scopus 로고
    • note
    • Most likely, in keeping with earlier proposals (see ref. [5]), the formation of allene 9 is the rate-determining step; therefore, 9 has never been observed in the reaction mixtures.
  • 35
    • 84985079237 scopus 로고
    • 4-catalyzed cycloisomerization of allenic alcohols into 2,5-dihydrofurans, see: a) L.-I. Olsson, A. Claesson, Synthesis 1979, 743;
    • (1979) Synthesis , pp. 743
    • Olsson, L.-I.1    Claesson, A.2
  • 36
    • 0001612307 scopus 로고
    • for the metal-catalyzed cyclization of allenyl ketones into furans, see: b) J. A. Marshall, X. Wang, J. Org. Chem. 1991, 56, 960;
    • (1991) J. Org. Chem. , vol.56 , pp. 960
    • Marshall, J.A.1    Wang, X.2
  • 41
    • 0034600902 scopus 로고    scopus 로고
    • f) A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382; Angew. Chem. Int. Ed. 2000, 39, 2285.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2285
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    • 4544253286 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for details.
  • 43
    • 0141843609 scopus 로고    scopus 로고
    • Potentially, furanyl tosylates can be used in cross-coupling reactions. For the Pd-catalyzed cross-coupling of aryl tosylates, see: a) H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11818
    • Nguyen, H.N.1    Huang, X.2    Buchwald, S.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.