Abstract
The reaction of sec-butyllithium with acrolein dialkyl acetals in THF or in THF/Et 2O/pentane at -95°C results in formation of gem-dialkoxyallyllithium reagents, Li[CH 2CHC(OR) 2]. These react with organosilicon and organotin chlorides to give ketene acetals, R 3SiCH 2CHC(OR) 2 and R 3SnCH 2CHC(OR) 2. The acid hydrolysis of these products produces β-substituted propionic acid esters, R 3SiCH 2CH 2CO 2R and R 3SnCH 2CH 2CO 2R. Reactions of these lithium reagents with allyl bromide gave esters of 5-hexonoic acid, CH 2CH(CH 2) 3CO 2R (R = Me, Et).
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