Stereoselective Synthesis of (Z)- and (E)-1,3-Alkadienes from Aldehydes Using Organotitanium and Lithium Reagents

Article abstract of DOI:10.1016/S0040-4020(01)90006-7

<3-(Diphenylphosphino)allyl>titanium reagent generated easily from allyldiphenylphosphine condenses with aldehydes to give (Z)-1,3-alkadienes in a highly regio- and stereoselective manner.In contrast, lithiated allyldiphenylphosphine oxide condenses with aldehydes to give (E)-1,3-alkadienes directly and stereoselectively in good yield.Similarly, lithiated (1-buten-3-yl)diphenylphosphine oxide condenses with aldehydes to give (E)-3-methyl-1,3-alkadienes.