New functional allylic lithium reagents: gem-dialkoxyallyllithium reagents: a useful route to β-silyl-and β-stannylpropionate esters

D Seyferth, RE Mammarella, HA Klein

文献索引：Seyferth, Dietmar; Mammarella, Robert E.; Klein, Helmut A. Journal of Organometallic Chemistry, 1980 , vol. 194, # 1 p. 1 - 8

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被引用次数: 22

摘要

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