Synthesis of optically active (E)-1-alkoxymethoxybut-2-enyl(tributyl)stannanes: stereochemistry of their thermal reactions with aldehydes

Abstract

(1R)- and (1S)-1-[(–)-Menthyloxymethoxy]-(E)-but-2-enyl(tributyl)stannanes (8) and (9), whose configurations were assigned by correlation with (2R)- and (2S)-pentan-2-ol (14) and (15), react stereoselectively on heating with benzaldehyde to give (3S,4S)- and (3R,4R)-4-hydroxy-3-methyl-(Z)-1,2-enol ethers (16) and (18), respectively, the configurations of these products being established by correlation with pseudoephedrine.