(<i>S</i>,<i>S</i>)-(<i>+</i>)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions

Organolithium reagents undergo highly regio- and diastereoselective 1,4-addition to (<i>S,S</i>)-(+)-pseudoephedrine enamides furnishing the corresponding β-alkyl-substituted adducts in excellent yields and diastereoselectivities. In addition, the intermediate lithium enolates generated after the conjugate addition step undergo a highly diastereoselective alkylation reaction, furnishing α,β-dialkyl-substituted amides in high yields. The obtained adducts have been converted into chiral nonracemic β-alkyl- and α,β-dialkyl-substituted carboxylic acids and γ-alkyl- and β,γ-dialkyl-substituted alcohols using very simple and high-yielding procedures.