Tandem asymmetric conjugate addition/α-alkylation using (S,S)-(+)-pseudoephedrine as chiral auxiliary

alpha,ss-Unsaturated amides derived from the chiral amino alcohol (S,S)-(+)-pseudoephedrine undergo a very clean and diastereoselective tandem conjugate addition/alpha-alkylation reaction. Excellent results have been achieved using a wide range of differently substituted conjugate acceptors, organolithium reagents, and alkyl halides. The chiral auxiliary could be easily removed from the obtained adducts by reduction, furnishing chiral nonracemic alpha,ss-branched alcohols in a very easy and efficient way.