Highly efficient synthesis of allylic alcohols having an α-alkoxyalkyl group at their β-position via regioselective addition reaction of titanium-propargyl ether complexes with carbonyl compounds

Article abstract of DOI:10.1016/0040-4039(96)01647-4

Diisopropoxytitanium-propargyl ether complexes 2, readily generated in situ from Ti(OPr(i)):4/ 2 (i)PrMgBr reagent and propargylic ethers 3, react with aldehydes and ketones highly regioselectively at the carbon having an α-alkoxyalkyl group, thus affording an efficient and practical method for synthesizing allylic alcohols 4 having an α-alkoxyalkyl group at the β-position. The synthesis of conjugated dienes 7h and 8h from the resulting 4h is also described.