Pseudoesters and derivatives. XXX. Synthesis of 5-substituted furan-2(5H)-ones by the regiospecific reaction of anions of enaminofuranones with electrophiles
作者： Begoña de Ancos , Francisco Fariñ , M.Carmen Maestro , M.Rosario Martin , M.Mercedes Vicioso
DOI: 10.1016/S0040-4020(01)96042-9
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摘要: Abstract Reactions of lithium enolates 2a,b derived from 5-methoxy(or 5-ethylthio)-4-(pyrrolidin-1-yl)- furan-2(5H)-ones (1a,b) with various electrophiles, such as alkylating agents, aldehydes, phenyl isocyanate, acyl chlorides, and trimethylsilyl chloride, occur regiospecifically to give the corresponding 5-substituted derivatives in synthetically useful yields.
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sci-hub.se 参考文章(32)
Okiko Miyata, Richard R. Schmidt, Kinetic Acidity of Methine Protons and Carbonyl-Activated Methylene Protons† Angewandte Chemie. ,vol. 21, pp. 637- 637 ,(1982) , 10.1002/ANIE.198206371
Richard C. Larock, Bernhard Riefling, Constance A. Fellows, Mercury in organic chemistry. 12. Synthesis of .beta.-chloro-.DELTA..alpha.,.beta.-butenolides via mercuration-carbonylation of propargylic alcohols Journal of Organic Chemistry. ,vol. 43, pp. 131- 137 ,(1978) , 10.1021/JO00395A031
Andrew Pelter, Redha Al-Bayati, Wynne Lewis, 2-trimethylsilyloxy-4-methoxyfuran: An excellent synthon for the production of 50substituted tetronates (40methoxybutenolides). Tetrahedron Letters. ,vol. 23, pp. 353- 356 ,(1982) , 10.1016/S0040-4039(00)86829-X
William R. Roush, Timothy A. Blizzard, Fatima Z. Basha, Methodology for the synthesis of the acyclic portions of verrucarins A and J Tetrahedron Letters. ,vol. 23, pp. 2331- 2334 ,(1982) , 10.1016/S0040-4039(00)87334-7
Emilio Quinoa, Ernest Kho, Lawrence V. Manes, Phillip Crews, Gerald J. Bakus, Heterocycles from the marine sponge Xestospongia sp Journal of Organic Chemistry. ,vol. 51, pp. 4260- 4264 ,(1986) , 10.1021/JO00372A029
John R. Donaubauer, Trevor C. McMorris, Synthesis of lepiochlorin, an antibiotic metabolite of a fungus cultivated by ants Tetrahedron Letters. ,vol. 21, pp. 2771- 2772 ,(1980) , 10.1016/S0040-4039(00)78602-3
Manat Pohmakotr, Prapanpong Jarupan, A new synthesis of α,β-unsaturated γ- and δ-lactones via intramolecular acylation of α-sulfinyl carbanion Tetrahedron Letters. ,vol. 26, pp. 2253- 2256 ,(1985) , 10.1016/S0040-4039(00)98975-5
David W Brown, Malcolm M Campbell, Anthony P Taylor, Xiao-an Zhang, Regio- and diastereoselectivity in aldol reactions of cyclopent-2-enone, 2-(5H)furanone and their derived trimethylsilyloxydienes Tetrahedron Letters. ,vol. 28, pp. 985- 988 ,(1987) , 10.1016/S0040-4039(00)95893-3
Yoshimitsu Nagao, Wei Min Dai, Masahito Ochiai, Motoo Shiro, New general asymmetric synthesis of versatile .gamma.-alkylated butenolides and its application to expeditious synthesis of the chiral Geissman-Waiss lactones useful for (+)-retronecine synthesis Journal of Organic Chemistry. ,vol. 54, pp. 5211- 5217 ,(1989) , 10.1021/JO00283A009
Y. S. Rao, Recent advances in the chemistry of unsaturated lactones Chemical Reviews. ,vol. 76, pp. 625- 694 ,(1976) , 10.1021/CR60303A004