Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers

An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary-tertiary stereocenters is summarized. The chiral copper(I)-phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in alpha-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.

Automated summary

An enantioselective approach for synthesizing fluorinated azaarenes with vicinal quaternary-tertiary stereocenters has been summarized, utilizing a chiral copper(I)-phosphine complex to bind with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in highly enantioselective compounds with excellent yields. Further functionalization of the acyl imidazole part has also been demonstrated.