Ester enolate Claisen rearrangement using a polymer-supported silyl triflate

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3289-3292

  Hu, Yonghang ^a,b   Porco Jr , John A ^a  

^a Argonaut Technologies   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; POLYMER; SILANE DERIVATIVE; SILYLTRIFLATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; REACTION ANALYSIS; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0033597250     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00441-4     Document Type: Article

References (26)

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12. 8 PS-DES resin is commercially available from Argonaut Technologies, San Carlos, CA.
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16. 2 (2 x 4 mL). The PS-DES silyl triflate resin was used immediately after generation.
17. 11 Bruce C. Hamper and Thomas J. Owen, Monsanto Company, 800 N. Lindbergh Blvd., St. Louis, MO, unpublished results.
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22. 3, 75 MHz): δ 170.50, 136.35, 133.91, 129.07, 128.34, 126.84, 116.32, 74.96, 41.42, 33.76, 31.14, 24.22, 22.12, 13.56. Yield: 90%, GC purity: 94%.
23. 3, 75 MHz): δ 176.37, 135.43, 116.40, 51.02, 39.29, 36.73, 35.30, 33.25, 32.59, 26.18, 25.85 ppm.
24. 15 Other acetic acid esters (e.g. geranyl acetate, linalyl acetate) were also used yielding similar results.
25. 16 Emde, H.; Simchen, G. Synthesis 1977, 867.
26. 17 Smith, E.M. Tetrahedron Lett. 1999, 40, see preceding paper.