Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary.

Graphical abstract Highlights • Design, synthesis and stereoselective study of a novel heterobifunctional chiral auxiliary. • Structure with two reaction sites that could give rise two distinct groups of opposite stereochemistry. • Highly programmable stereoselective nucleophilic and electrophilic additions. • Potential access to tertiary alcohols and derivatives in high optical purity. Abstract The synthesis and diastereoselective performance of the pseudo C 2 -symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary. [ABSTRACT FROM AUTHOR]