Litcius/Paper detail

Chiral phosphoric acid-catalyzed dual-ring formation for enantioselective construction of N–N axially chiral 3,3′-bisquinazolinones

Liang-Yuan Pu, Yujiao Zhang, Wei Liu, Fan Teng

2022Chemical Communications43 citationsDOI

Abstract

In contrast with the well-developed C-C and C-N axial chirality, research focusing on the catalytically asymmetric synthesis of N-N axially chiral compounds is still limited. As a privileged subunit of many antibiotics, the synthesis of N-N axially chiral 3,3'-bisquinazolinones has not been updated with atroposelective construction. Herein, we firstly report a chiral phosphoric acid-catalyzed dual-ring formation strategy leading to the aforementioned compounds with good chemical yields and enantioselectivities. Notably, metal-free reaction conditions are another advantage of this procedure.

Topics & Concepts

Axial symmetryEnantioselective synthesisPhosphoric acidAxial chiralityRing (chemistry)CatalysisChirality (physics)ChemistryCombinatorial chemistryDual (grammatical number)StereochemistryComputational chemistryOrganic chemistryChiral symmetryPhysicsQuantum mechanicsLiteratureNambu–Jona-Lasinio modelQuarkArtAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling