Journal of Organic Chemistry p. 1628 - 1631 (1990)
Update date:2022-07-29
Topics: Ester Homoenolates Carbonyl Compounds lanthanoid Metals 3-Halo Esters Homo-Reformatsky-type reaction
Fukuzawa, Shin-ichi
Sumimoto, Norifumi
Fujinami, Tatsuo
Sakai, Shizuyoshi
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 γ-lactones in good yields under mild conditions.The isolation of 3-phenylseleno (8a), 3-phenyltelluro (8b), and 3-tri-n-butylstannyl esters (10) from the reaction with diphenyl diselenide (7a), ditelluride (7b), and tri-n-butyltin iodide (9), respectively, suggests the formation of the lanthanoid ester homoenolate.
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