Stereoregulations of Pyrimidinone Based Chiral Auxiliary in Aldol and Alkylation Reactions: A Convenient Route to Oxyneolignans

(S)-4-Isopropyl-1-phenyltetrahydropyrimidin-2(1H)-one was synthesized and evaluated as a chiral auxiliary for asymmetric acetate and propionate aldol reactions, by generation of titanium and lithium enolates, affording excellent yields and stereoselectivities for syn and anti aldol diastereomers, respectively. High stereoselectivities were also obtained in lithium mediated alkylation reactions. The application of the auxiliary was exemplified in the asymmetric synthesis of a natural oxyneolignan, (+)-(7S,8S)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneoligna-7,9-diol-7′-oic acid.