The cyanide catalyzed isomerization of enol esters derived from cyclic 1,3-diketones

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1007-1010

  Montes, Imber Flores ^a   Burger, Ulrich ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; PYOLUTEORIN; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030062842     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02362-3     Document Type: Article

References (28)

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12. c) In a typical experiment, a solution of 10 mmol of 3 (R = alkyl), 3 ml of triethylamine, 10 mg of potassium cyanide (or 100 ml of acetone cyanohydrin) in 25 ml of acetonitrile was stirred for 12 h at room temperature. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and 1N hydrochloric acid (hood: HCN!). The triketone 4 was then extracted from the organic layer into aqueous sodium bicarbonate. Neutralization and extraction with ether gave, after drying and concentration, the crude product that was chromatographed.
13. Review: T. H. Black 'Recent Progress in the Control of Carbon versus Oxygen Acylation of Enolate Anions' Organic Preparations and Procedures (Newton Highlands, MA) 1989, 21, 179-217.
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20. 13C-NMR spectra consistent with the structures indicated.
21. 3, 50 MHz): 28.2 (q); 33.3 (s); 42.3 (t); 50.9 (t); 56.0 (q); 112.2 (d); 116.8 (s); 117.9 (s); 120.2 (d); 132.3 (d); 135.0 (d); 160.2 (s); 162.3 (s); 168.8 (s); 199.4 (s).
22. 3, 50 MHz): 28.2 (q); 30.9 (s); 45.9 (t); 51.7 (t); 55.4 (q); 110.7 (d); 114.1 (s); 120.6 (d); 128.2 (d); 128.9 (s); 132.0 (d); 156.5 (s); 193.7 (s); 193.8 (s); 196.4 (s).
23. Note: Simple enol esters derived from monoketones do not react in analogous fashion. Normally, they are not cleaved by cyanide.
24. G.A. Olah, M. Arvanaghi, G.K. Surya Prakash, Synthesis, 1983, 636-637.
25. 3, 100 MHz): 19.0 (t); 36.2 (t); 39.7 (t); 110.5 (s); 112.5 (d); 122.1 (d); 126.8 (d); 128.3 (s); 179.3 (s); 197.1 (s); 204.1 (s).
26. 3, 100 MHz): 102.4 (d); 114.1 (d); 114.3 (s); 114.6 (d); 115.9 (d); 120.6 (d); 131.5 (s); 136.5 (d); 143.0 (s); 156.9 (s); 182.0 (s)
27. a) A. Bohac, P. Hrnciar, Synthesis, 1991, 881-882;
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