Milieux hyperbasiques : Nouvelle méthode de synthèse de γ et δ-cétoaldéhydes
作者： M. Larchevêque , G. Valette , Th. Cuvigny
DOI: 10.1016/0040-4020(79)88003-5
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摘要: Abstract Substituted γ and δ-ketoaldehydes may be conveniently synthesized in two steps from imine carbanions, which are obtained by reaction with hyperbasic media. These anions stable at low temperature (−30°); they react functional electrophiles to afford masked ketoaldehydes cyclised into various cyclopentenones or cyclohexenones.
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P. Bosshard, C.H. Eugster, The development of the chemistry of furans, 1952-1963* Advances in Heterocyclic Chemistry. ,vol. 7, pp. 377- 490 ,(1967) , 10.1016/S0065-2725(08)60594-2
A. I. Meyers, Nicholas Nazarenko, Dihydro-1,3-oxazines. XVI. General synthesis of 2-alkylcyclopentenones and a method for adding CH2CO2Me to electrophilic olefins. Application to the synthesis of methyl jasmonate Journal of Organic Chemistry. ,vol. 38, pp. 175- 176 ,(1973) , 10.1021/JO00941A047
Herbert O. House, Martin Gall, Hugh D. Olmstead, Chemistry of carbanions. XIX. Alkylation of enolates from unsymmetrical ketones Journal of Organic Chemistry. ,vol. 36, pp. 2361- 2371 ,(1971) , 10.1021/JO00815A037
Evan Baltazzi, Lewis I. Krimen, Recent Advances in the Chemistry of Pyrrole. Chemical Reviews. ,vol. 63, pp. 511- 556 ,(1963) , 10.1021/CR60225A004
M. F. Ansell, S. S. Brown, 602. Reduced cyclic compounds. Part IV. The intramolecular acylation of some olefinic acids Journal of the Chemical Society (Resumed). pp. 2955- 2961 ,(1958) , 10.1039/JR9580002955
M. F. Ansell, J. W. Ducker, 59. Reduced cyclic compounds. Part VII. A new route to 2-substituted cyclopent-2-enones Journal of The Chemical Society (resumed). pp. 329- 331 ,(1959) , 10.1039/JR9590000329
Marc LARCHEVÊQUE, Gérard VALETTE, Thérèse CUVIGNY, Hyperbasic Media; Synthesis of 1-Alkyl-3-oxocyclohexenes from 1,5-Diketones Synthesis. ,vol. 1977, pp. 424- 427 ,(1977) , 10.1055/S-1977-24428
Hans Meerwein, Über 1,5‐Dialdehyde und 1,5‐Ketonaldehyde und deren Umlagerung in δ‐Lactone; Konstitution und Bildungsweise der Amarsäure, Diäthylcarbobenzonsäure und verwandter Verbindungen. Allgemeiner Teil Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 97, pp. 225- 237 ,(1918) , 10.1002/PRAC.19180970113
M. LARCHEVEQUE, G. VALETTE, T. CUVIGNY, H. NORMANT, Hyperbasic Media: Metalation of Ketimines; a Fast Convenient Synthesis of 1,4-Diketones Synthesis. ,vol. 1975, pp. 256- 259 ,(1975) , 10.1055/S-1975-23722
R.D. Allan, B.G. Cordiner, R.J. Wells, Bridged bicyclic ring systems from 3-(2′-oxocycloalkyl) propanals produced via enamines Tetrahedron Letters. ,vol. 9, pp. 6055- 6056 ,(1968) , 10.1016/S0040-4039(00)70791-X