Naslov
Stereoselective Synthesis of α-Quaternary Methaneamines via Formal Betti Reaction Catalyzed by Chiral Brønsted Phosphoric Acid

Autori
Beriša, Arben ; Gredičak, Matija

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, neobjavljeni rad, ostalo

Skup
21st Tetrahedron Symposium

Mjesto i datum
Göteborg, Švedska; online, 21.06.2021. - 24.06.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Podatak o recenziji nije dostupan

Ključne riječi
stereoselektivna sinteza ; kvaterni stereogeni centar ; organokataliza
(stereoselective synthesis ; quaternarny stereogenic center ; organocatalysis)

Sažetak
Chiral α-quaternary methanamines are common structural motifs found in a variety of natural products exhibiting wide spectrum of biological activities. Synthesis of such compounds has always been challenging because of the steric hindrance positioned at the newly formed center of chirality. The most common strategies for the construction of this class of optically active compounds is well described and mostly relies on usage of chiral transition-metal complexes, e.g. Rh(I), Pd(II), Ni(II), and Co(II). However, to the best of our knowledge, there is no literature precedent for the preparation of quaternary α- triarylsubstituted methanamines based on stereoselective organocatalytic reaction. In this respect, we developed a catalytic formal Betti reaction with stereoselctivity induced by chiral Brønsted phosphoric acid. This type of reaction proceeds via direct 1, 2-addition of phenols to imines resulting in enantioenriched α- triarylmethanamines. Key to success of this transformation lies in the in situ generation of the reactive iminium species from 3- hydroxysubstituted isoindolinones. Various phenols added smoothly, enabling the synthesis of a variety of α-triphenylmethylamines in up to 96% isolated yield, and up to 99% ee. Functional group tolerance with respect to isoindolinone alcohols, as well as to phenols, will be presented.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA