Tetrahedron

Dilithiated 3-tosylpropanal dimethyl acetal as β, β-acylvinyl dianion or homoenolate dianion equivalent

P Bonete, C Nájera

Index: Bonete, Pedro; Najera, Carmen Tetrahedron, 1996 , vol. 52, # 11 p. 4111 - 4122

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Citation Number: 15

Abstract

3, 3-Dilithio-1, 1-dimethoxy-3-tosylpropane (6) reacts with mono and dielectrophiles to give dialkylated products 7 and carbocyclic derivatives 8, respectively. Hydrolysis of the acetal function followed by DBU dehydrosulfinylation of these products affords β, β-disubstituted propenal derivatives 11 and 12. Reductive desulfonylation of compounds 8g-j provides β, β- disubstituted propanal acetals 14.

~92%

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