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Stereoselective thermal reactions between (E)-1-alkoxymethoxybut-2-enyl-(tributyl)stannanes and aldehydes
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1989
Year
Trans-4,5-disubstituted ButyrolactonesStereoselective Thermal ReactionsChloromethyl Methyl EtherOrganic ChemistryAnti-4-hydroxy-3-methyl-cis-1,2-enol EthersStereoselective SynthesisChemistryPharmacologySynthetic ChemistryEnantioselective Synthesis
(E)-1-Methoxymethoxybut-2-enyl(tributyl)stannane (6), readily available by the addition of tributylstannyl-lithium to crotonaldehyde and alkylation of the adduct using chloromethyl methyl ether, reacts on heating with aldehydes to give anti-4-hydroxy-3-methyl-cis-1,2-enol ethers. These on hydrolysis and oxidation provide trans-4,5-disubstituted butyrolactones.