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Volumn 46, Issue 38, 2005, Pages 6429-6432

Reaction of δ-silyl-γ,δ-epoxy-α,β-unsaturated acylsilanes with cyanide ion: Possibility of the formation of silicate intermediate in anion-induced ring opening of epoxysilanes

Author keywords

Allyl silanes; Brook rearrangement; Electrophilic substitution; Epoxysilanes; Tandem reactions

Indexed keywords

CYANIDE; SILANE DERIVATIVE; SILICATE;

EID: 23844544536     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.120     Document Type: Article
Times cited : (20)

References (35)
  • 2
    • 33645332652 scopus 로고    scopus 로고
    • note
    • 2Et resulted in the formation of an O-carbamoyl derivative.
  • 3
    • 0001622693 scopus 로고
    • For discussions on stereochemistry in the reactions in which enol silyl ethers are formed from α-silyl alkoxides bearing a β-leaving group via the Brook rearrangement, see: H.J. Reich, R.C. Holtan, and C. Bolm J. Am. Chem. Soc. 112 1990 5609 5617
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5609-5617
    • Reich, H.J.1    Holtan, R.C.2    Bolm, C.3
  • 6
    • 33645349088 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, there is no precedent for a stereochemical discussion concerning Brook rearrangement in α-silyl allylalkoxides.
  • 10
    • 0035835953 scopus 로고    scopus 로고
    • For the use of the Brook rearrangement in tandem bond formation strategies, see: W.H. Moser Tetrahedron 57 2001 2065 2084
    • (2001) Tetrahedron , vol.57 , pp. 2065-2084
    • Moser, W.H.1
  • 16
    • 33645336863 scopus 로고    scopus 로고
    • note
    • 3; Z = 4; R = 0.0702.
  • 18
    • 0000024039 scopus 로고    scopus 로고
    • Hypervalent Silicon Compounds
    • Z. Rappoport Y. Apeloig Wiley Chichester, UK
    • For reviews of hypervalent silicon compounds, see: D. Kost, and I. Kalikhman Hypervalent Silicon Compounds Z. Rappoport Y. Apeloig The Chemistry of Organic Silicon Compounds Vol. 2 1998 Wiley Chichester, UK Chapter 23
    • (1998) The Chemistry of Organic Silicon Compounds , vol.2
    • Kost, D.1    Kalikhman, I.2
  • 27
    • 0344391973 scopus 로고    scopus 로고
    • We have previously reported the possibility that C-O bond cleavage and Si-O bond formation in base-promoted ring opening of metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehydes proceed in a concerted manner. See: M. Sasaki, E. Kawanishi, E. Nakai, T. Matsumoto, K. Yamaguchi, and K. Takeda J. Org. Chem. 68 2003 9330 9339
    • (2003) J. Org. Chem. , vol.68 , pp. 9330-9339
    • Sasaki, M.1    Kawanishi, E.2    Nakai, E.3    Matsumoto, T.4    Yamaguchi, K.5    Takeda, K.6
  • 32
    • 33645377560 scopus 로고    scopus 로고
    • note
    • Treatment of 3 with KHMDS (1.1 equiv) in the presence of MeI and 18-crown-6 (0.05 equiv) in THF at 0°C for 5 min, conditions that roughly mimic those which can be encountered in the reaction from 1a, resulted in the formation of 4 (52% yield; E/Z = 1/2.5) and protonated derivative 2 (El = H) (28% yield; E/Z = 1/6.7).
  • 33
    • 33645336585 scopus 로고    scopus 로고
    • note
    • 2Et provided (5E)-10a in 93% yield. See Ref. 1.
  • 34
    • 33645338482 scopus 로고    scopus 로고
    • note
    • The use of less bulky silyl groups such as trimethylsilyl and dimethylphenylsilyl resulted in the hydrolysis of the enol silyl ether to the corresponding aldehydes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.