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Volumn 121, Issue 51, 1999, Pages 12208-12209

A stereoelectronic model to explain the highly stereoselective reactions of nucleophiles with five-membered-ring oxocarbenium ions [13]

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; OXOCARBENIUM; UNCLASSIFIED DRUG;

EID: 0033616106     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993349z     Document Type: Letter
Times cited : (242)

References (36)
  • 8
    • 0031575589 scopus 로고    scopus 로고
    • For a recent application of Reissig's model, see: Alonso, E.; Ramon, D. J.; Yus, M. Tetrahedron 1997, 53, 2641-2652.
    • (1997) Tetrahedron , vol.53 , pp. 2641-2652
    • Alonso, E.1    Ramon, D.J.2    Yus, M.3
  • 11
    • 0000693134 scopus 로고
    • Other reactions of acetals do not appear to involve free cations: (c) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089-8110).
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8089-8110
    • Denmark, S.E.1    Almstead, N.G.2
  • 21
    • 0343836200 scopus 로고    scopus 로고
    • note
    • The details are provided as Supporting Information.
  • 22
    • 0343400464 scopus 로고    scopus 로고
    • note
    • Control experiments for the acetals 3 and 9, for which the two anomers of starting material are separable, indicate that both anomers give the same product with the same degree of selectivity. Stereoselectivities depend on Lewis acid to only a minor extent.
  • 24
    • 0343836199 scopus 로고    scopus 로고
    • note
    • Allylation of the tetrahydrofuran acetate with a benyloxymethyl group at C-4 provided a 67:33 mixture of diastereomeric products.
  • 25
    • 0342965263 scopus 로고    scopus 로고
    • note
    • 2O-substituted acetates. The stereo-chemistry was proven to be 1,3-cis for the silyloxy-substituted substrate.
  • 29
    • 0342965261 scopus 로고    scopus 로고
    • note
    • Preliminary computational studies suggest that although both oxocarbenium ions 17 and 19 are of comparable energy, the product 20 derived from 19 should be strongly destabilized by this 1,3-diaxial interaction.
  • 31
    • 0032473853 scopus 로고    scopus 로고
    • This counter-intuitive conformational preference has been invoked to explain stereoselective reactions of acetoxy-substituted vinyloxocarbenium ions: Hosokawa, S.; Kirschbaum, B.; Isobe, M. Tetrahedron Lett. 1998, 39, 1917-1920.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1917-1920
    • Hosokawa, S.1    Kirschbaum, B.2    Isobe, M.3
  • 34
    • 0342530997 scopus 로고    scopus 로고
    • note
    • Preliminary ab initio calculations suggest that the diaxial conformer 21 is the only energy minimum of this cation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.