1-Ethoxyvinyl lithium

The heptodialdose 5 was synthesized from cycloheptatriene by osmylation of its iron tricarbonyl complex and ozonolysis. Addition of 1-ethoxyvinyl-lithium to the lactone 6 and subsequent acid hydrolysis has afforded Udeoxy-u-erythro-hex-2,3-diulose (7). ... 

Schlosser, M. Wei, H.-X. 2-Ethoxyvinyl-lithiums and diefhoxyvinyllithiums what makes them stable or fragile Tetrahedron 1997, 53, 1735-1742. 

In another series of experiments, we found that the reaction of N3P3F3C(OC2H )=CH2 with dimethylamine leads to the non-geminal isomers, 2,4-N3P3FA[N(CH3)2]C(OC2H3)=CH2 the same product is obtained from the reaction of ethoxyvinyl lithium with dimethyl-aminopentafluorocyclotriphosphazene. 

Acyldihydrocodeinones (146) were made in a similar manner. The 8/3-(trans-1 -oxo-2-butenyl)- and 8/3-benzoyl derivatives were prepared from protected acyl lithium cuprates, and the 8/3-methylcarbonyl- (146) from the lithium bis(a-ethoxyvinyl) cuprate with codeinone, followed by mild hydrolysis of the intermediate, 147. Preparation of 8/3-t-alcohols may be achieved from 147 after reduction of the ring carbonyl, treatment with an appropriate alkyl lithium to 148, and oxidation back to a ketone, 149. 

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