87444-58-4Relevant academic research and scientific papers
A Highly Stereoselective Synthesis of (E)-Enol Lactones by the Wittig Reaction of Cyclic Anhydrides with (α-Alkoxycarbonylethylidene)triphenylphosphorane
Tsuboi, Sadao,Fukumoto, Hirohumi,Wada, Hiroshi,Takeda, Akira,Fukuyama, Keiichi
, p. 689 - 696 (2007/10/02)
Reactions of glutaric anhydride and methyl- or phenyl-substituted ones with (α-alkoxycarbonylethylidene)triphenylphosphorane (2a, ethoxy; 2b, t-butoxy) gave the corresponding 6-alkoxycarbonyl-5-hepten-5-olides (3) and 6-alkoxycarbonyl-4-hepten-5-olides in good yields.The reaction proceeded highly stereoselectively to give (E)-3.The stereochemistry of 3 was determined by an X-ray crystallographic analysis.The reaction of adipic anhydride with 2a afforded 7-ethoxycarbonyl-5-octen-6-olide, 7-ethoxycarbonyl-5,6-octadienoic acid, and (4E,6E)-7-ethoxycarbonyl-4,6-octadienoic acid.A treatment of nonanedioic anhydride with 2a gave 10-ethoxycarbonyl-8,9-undecadienoic acid, (7E,9E)-10-ethoxycarbonyl-7,9-undecadienoic acid, and diethyl 2-methyl-2,4-undecadienedioate in low yields.
A HIGHLY STEREOSELECTIVE SYNTHESIS OF ENOL-δ-LACTONES BY THE WITTIG REACTION OF GLUTARIC ANHYDRIDES WITH α-ALKOXYCARBONYLETHYLIDENETRIPHENYLPHOSPHORANE
Tsuboi, Sadao,Fukumoto, Hirohumi,Takeda, Akira
, p. 1219 - 1220 (2007/10/02)
Enol-δ-lactones were prepared stereoselectively by the title reaction.
