Asymmetric Alkylation of Amide Anions. Product Analysis by GLC Using Cholesteryl Cinnamate, a Liquid Crystal Phase.

Article abstract of DOI:10.1021/jo01303a046

Chiral Amides derived from (S)-(-)-prolinol and its methyl ether were metalated and alkylated to afford α-alkyl amides in 12-82percent ee.The configuration induced by (S)-(-)-prolinol, as the chiral auxiliary reagent, was opposite to that induced by its methyl ether.Diastereomer composition of the alkylated products were readily, in fact, uniquely, assessed by GLC by using a capillary column coated with cholesteryl cinnamate.