Practical Synthesis of Two Different Pseudoenantiomeric Organocatalysts with cis-Cyclohexanediamine Structure from a Common Chiral Source

Abstract

An approach has been developed for the practical synthesis of two different, structurally robust, pseudoenantiomeric amino Tf-amido organocatalysts with a cis-1,2-cyclohexanediamine structure. These pseudoenantiomeric organocatalysts, which are very useful for the practical synthesis of both enantiomeric aldol products, are easily prepared from commercially available cis-4-cyclohexene-1,2-dicarboxylic acid in a four-step sequence. The Diels–Alder strategy of 2-alkyl-1,3-butadiene and maleic anhydride would provide a general approach to the facile synthesis of various pseudoenantiomeric organocatalysts.