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

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.