Direct preparation of lanthanoid ester homoenolates from 3-halo esters and lanthanoid metals: their homo-Reformatskii type reaction with carbonyl compounds

S Fukuzawa, N Sumimoto, T Fujinami…

文献索引：Fukuzawa, Shin-ichi; Sumimoto, Norifumi; Fujinami, Tatsuo; Sakai, Shizuyoshi Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1628 - 1631

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被引用次数: 26

摘要

The direct reaction of ethyl 3-bromopropionate (2a) or 3-iodopropionate (2b) with lanthanoid metals (La, Ce, Nd, Sm) in tetrahydrofuran produces lanthanoid ester homoenolates (3), which react with ketones to give y-lactones in good yields under mild conditions. The isolation of 3-phenylseleno@ a), 3-phenyltelluro (ab), and 3-tri-nbutylstannyl esters (10) from the reaction with diphenyl diselenide (7a), ditelluride (7b), and tri-n-butyltin iodide (9), ...