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On the use of E-1-methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-selective, homo-enolate equivalent
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1982
Year
Enantioselective SynthesisThreo-4,5-disubstituted ButyrolactonesChloromethyl Methyl EtherOrganic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryPharmacologyAsymmetric CatalysisSynthetic ChemistryAliphatic AldehydesHomo-enolate EquivalentNatural Product Synthesis
(E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyllithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4,5-disubstituted butyrolactones.