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Volumn , Issue 4, 1998, Pages 413-415

Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates. A comparative study with lithium enolates

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EID: 0002858730     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1668     Document Type: Review
Times cited : (7)

References (51)
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    • Benjamin W.A.; Menlo Park: California, 2nd ed.
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    • (1972) Modern Synthetic Reactions , pp. 492-570
    • House, H.O.1
  • 3
    • 26844500261 scopus 로고
    • Morisson, J.P. Ed Academic Press: New York
    • Heathcock, C.H. Asymmetric Synthesis vol. 3, Morisson, J.P. Ed Academic Press: New York, 1984, 1-110.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 1-110
    • Heathcock, C.H.1
  • 24
    • 0002563073 scopus 로고
    • Wiley: New York
    • Posner, G.H. Org. React, Wiley: New York, 1972, 19, 1-113.
    • (1972) Org. React , vol.19 , pp. 1-113
    • Posner, G.H.1
  • 33
    • 26844569407 scopus 로고    scopus 로고
    • note
    • 13C NMR : 22.7; 25.1; 27.2; 35.3; 39.3; 39.8; 56.7; 214.4. MS (m/z) : 152, 111, 95, 81, 67, 55.
  • 34
    • 26844459497 scopus 로고    scopus 로고
    • note
    • (Chemical Equation Presented)
  • 36
  • 37
    • 26844469283 scopus 로고    scopus 로고
    • note
    • The reaction of 2-methylcyclohexanone potassium enolates prepared from ketone 1b (tBuOK (1 eq.), THF, -20°C, 1h) with benzyl bromide (THF, -78°C, 1h) yielded ketone 8b (R = benzyl) with a 38% chromatographed yield. The regioisomeric ketone 9b (R = benzyl) was not detected. A large amount of unreacted ketone Ia was detected by GC in the erode material.
  • 38
    • 26844503639 scopus 로고    scopus 로고
    • note
    • 5 enolates obtained from silyl enol ethers, the alkylation is reported to maintain the structure of the starting silyl enol ether due to the enhanced nucleophilicity of these naked enolates, compared with lithium enolates. The alkylation conditions are also to be noted : the onium enolates are not preformed but obtained in the presence of the alkylating reagent, thus trapped as soon as they are formed, preventing proton transfer and their equilibration before alkylation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.