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Volumn 6, Issue 24, 2004, Pages 4495-4498

Formal [3 + 2] and [3 + 3] additions of acceptor-substituted cyclopropylmethylsilanes to allenylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM CHLORIDE; CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; METHYL GROUP; PHENYL GROUP; SILANE DERIVATIVE; TITANIUM TETRACHLORIDE;

EID: 10044244962     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047991w     Document Type: Article
Times cited : (54)

References (47)
  • 1
    • 10044241080 scopus 로고    scopus 로고
    • Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim
    • (a) Miura, K.; Hosomi, A. Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 409-501.
    • (2004) Main Group Metals in Organic Synthesis , vol.2 , pp. 409-501
    • Miura, K.1    Hosomi, A.2
  • 24
    • 0032900270 scopus 로고    scopus 로고
    • Wiley: London
    • For discussions on silyl-stabilized β-carbocations, see: (a) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (b) Lambert, J. B. Tetrahedron 1990, 46, 2627. (c) Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183.
    • (1976) Frontier Orbitals and Organic Chemical Reactions , pp. 81
    • Fleming, I.1
  • 25
    • 0032900270 scopus 로고    scopus 로고
    • For discussions on silyl-stabilized β-carbocations, see: (a) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (b) Lambert, J. B. Tetrahedron 1990, 46, 2627. (c) Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183.
    • (1990) Tetrahedron , vol.46 , pp. 2627
    • Lambert, J.B.1
  • 26
    • 0032900270 scopus 로고    scopus 로고
    • For discussions on silyl-stabilized β-carbocations, see: (a) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. (b) Lambert, J. B. Tetrahedron 1990, 46, 2627. (c) Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 183
    • Lambert, J.B.1    Zhao, Y.2    Emblidge, R.W.3    Salvador, L.A.4    Liu, X.5    So, J.-H.6    Chelius, E.C.7
  • 27
    • 10044294336 scopus 로고    scopus 로고
    • note
    • Cyclopropane derivatives 1a-c, 16, and 20 were prepared from a rhodium-catalyzed carbene insertion reaction of the corresponding diazocompound with allyl tert-butyldiphenylsilane.
  • 39
    • 10044283583 scopus 로고    scopus 로고
    • note
    • The assignment of the relative stereochemistry of 17-19, 21, and 22 by NOE measurements was difficult because of the crowded nature of the spectrum. Efforts are being made to secure the same through derivatization and crystal structure illucidation.
  • 40
    • 10044249384 scopus 로고    scopus 로고
    • note
    • 2O (2 x 5 mL). The combined organic extracts were washed with brine, dried, and concentrated. Purification of the residue by silica gel column chromatography (EtOAc/hexanes) furnished the pure product(s). The separation of the cis- and trans-isomers was achieved by radial chromatography over silica gel (EtOAc/hexanes).
  • 41
    • 10044243105 scopus 로고    scopus 로고
    • note
    • 2O (2 x 5 mL). The combined organic extracts were washed with brine, dried, and concentrated. Purification of the residue by silica gel column chromatography (EtOAc/hexanes) furnished the pure product.


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