Highly Diastereoselective Addition of Grignard Reagents to Aliphatic, Enolizable N-Alkylketimines and 2,2-Disubstituted 1,3-Oxazolidines. Asymmetric Synthesis of the Antidepressant Cericlamine

Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2-disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.