Generation of ketone dilithio α, β-dianions and their reactions with electrophiles

H Nakahira, M Ikebe, Y Oku, N Sonoda, T Fukuyama…

Index: Nakahira, Hiroyuki; Ikebe, Masanobu; Oku, Yoshiaki; Sonoda, Noboru; Fukuyama, Takahide; Ryu, Ilhyong Tetrahedron, 2005 , vol. 61, # 13 p. 3383 - 3392

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Citation Number: 6

Abstract

Ketone dilithio α, β-and α, β′-dianions can be generated by a tin–lithium exchange reaction of the lithium enolate of β-tributyltin substituted ketones. A chelation-aided approach, which employs β-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone α, β-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles.