On the use of E-1-methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-selective, homo-enolate equivalent

Authors:
  • APAndrew J. Pratt
    Andrew J. Pratt
  • ETEric J. Thomas
    Eric J. Thomas
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Abstract
(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.