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Tetrahedron Letters
Volumn 15, Issue 49-50, 1974, Pages 4319-4322
Peracid oxidation of trimethylsilyl enol ethers: A facile α-hydroxylation procedure
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Indexed keywords

EID: 0000626006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)92153-7     Document Type: Article
Times cited : (378)
References (19)
  • 2
    • 0000732727 scopus 로고
    • For a general review on the preparation of α-hydroxy ketones (acyloins) see:
    • (1948) Org. React. , vol.4 , pp. 256
    • McElvain1
  • 8
    • 33947300284 scopus 로고
    • Compounds 1a–1d were prepared by the general method outlined in:, In this manner, 1a–1d were obtained in yields ranging from 75–80%.
    • (1969) J. Org. Chem. , vol.34 , pp. 2324
    • House1    Czuba2    Gall3    Olmstead4
  • 9
    • 84917974610 scopus 로고    scopus 로고
    • The ir, nmr, and mass spectral properties of the compound are in accord with the structure proposed.
  • 10
    • 84917974609 scopus 로고    scopus 로고
    • In a typical oxidation, a solution of 10mm of MCPBA in 35ml of dry hexane was cooled in an ice methanol bath and treated with a solution containing 10mm of 1 in 15ml of hexane. After addition was complete(ca 5min), the resulting slurry was stirred for 45min. The slurry was then filtered to remove m-chlorobenzoic acid and the filtrate concentrated. The residue was then hydrolyzed, as indicated in Table I, or distilled to afford compounds of type 4.
  • 13
    • 84984281572 scopus 로고
    • Conversion of Endiol Bis-trimethylsilyl Ethers to Enolizable α-Diketones by Reaction with Bromine
    • Compound 2d was identical (ir,nmr, tlc retention time) to 2d prepared by the following sequence: Bromination of 1d by the method of
    • (1971) Synthesis , vol.1 , pp. 211
    • Strating1    Reiffers2    Wynberg3
  • 15
    • 0003592858 scopus 로고
    • For a concise summary see:, W.A. Benjamin, Inc, Menlo Park, California, and the references cited therein.
    • (1972) Modern Synthetic Reactions , pp. 302
    • House1
  • 16
    • 84917974607 scopus 로고    scopus 로고
    • Compound 4a showed the following additional properties: nmrδ-0.07(s,9H), 1.50(m,8H), 2.28(m,2H),4.18(m,1H); mass spectrum m/e200. Compound 4b showed the following additional properties: nmrδ 0.08(s,9H), 1.59(s,6H), 7.40(m,3H), 8.26(m,2H); mass spectrum m/e236. The fact that 4a could be converted cleanly to 2b, and 4b could be cleanly converted to 2d also serves as verification for the structures proposed for 4a and 4b.
  • 18
    • 0040078306 scopus 로고
    • For a recent discussion concerning silicon d-orbital participation during migration to oxygen see:, and the references cited therein.
    • (1974) J. Amer. Chem. Soc. , vol.96 , pp. 3012
    • Pinnavaia1    McClarin2

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.