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

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 a...

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Bibliographic Details
Published in:Tetrahedron 1996-03, Vol.52 (11), p.4111-4122
Main Authors: Bonete, Pedro, Nájera, Carmen
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)00072-5