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Volumn 36, Issue 17, 1995, Pages 2987-2990

Stereoselective synthesis of substituted tetrahydrofurans via selenoetherification of 2-silyl-3-alkenols. A study of allylic stereocontrol

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

EID: 0028920546     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)00410-E     Document Type: Article
Times cited : (46)

References (33)
  • 4
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    • Halocyclization of Unsaturated Alcohols and Carboxylic Acids Using Bis(sym-collidine)iodine(I) Perchlorate
    • (1988) Synthesis , pp. 862-868
    • Evans1    Magee2    Schauble3
  • 21
    • 84914025223 scopus 로고    scopus 로고
    • 4, EtOH, RT, 1h, 91% yield). The stereochemistries of 12 and 13 were assigned unambiguously using difference nOe experiments.
  • 23
    • 84914025222 scopus 로고    scopus 로고
    • An overlapping between the σ-CSi bond and the LUMO formed by the olefin and the incoming electrophile might be at the origin of this conformational preference.
  • 24
    • 84914025221 scopus 로고    scopus 로고
    • 2a
  • 31
    • 0027448716 scopus 로고
    • 2Si group cannot be oxidized in the presence of double bonds, due to the incompatibility of this function with the electrophilic conditions required for the oxidation. Other solutions to this problem have been proposed recently, see:
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7287-7290
    • Fleming1    Winter2
  • 32
    • 84944638447 scopus 로고
    • A Synthetic Approach to the C26-C32 Fragment of Rapamycin. A Synthesis of Allylic Alcohols from Allylic Furylsilanes.
    • (1994) Synlett , pp. 77-78
    • Norley1    Kocienski2    Faller3
  • 33
    • 0000999169 scopus 로고
    • A similar approach has been proposed by Stork with the furyldimethylsilyl group, see:, 5-Methylthienyl group was generally found to be more stable with our reaction conditions. We gratefully acknowledge Prof. G. Stork (Columbia University) for providing us with experimental details concerning the nucleophilic displacement of the furyl group.
    • (1989) Pure & Appl. Chem. , vol.61 , pp. 439-442
    • Stork1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.