Asymmetric 1,4-addition of Grignard reagents to chiral α,β-unsaturated imides in the presence of Lewis acids

Article abstract of DOI:10.1016/0957-4166(96)00163-2

The asymmetric 1,4 addition of PhMgCl, MeMgBr and allylMgBr to chiral imides 1 has been studied under various conditions. The presence of a Lewis acid, as AlMe₂Cl, affords an enhanced diastereoselectivity favouring the formation of the product derived from the attack on the re face. The 1,4 addition of allyl diisopropoxyborate to imides 1 has also been analysed.