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Recent Advances in Catalytic Atroposelective Construction of Pentatomic Heterobiaryl Scaffolds

Xiao‐Long He, Cheng Wang, You‐Wu Wen, Zhouyu Wang, Shan Qian

2021ChemCatChem61 citationsDOI

Abstract

Abstract Pentatomic heterobiaryl performs as a key structural motif in various natural products and bioactive compounds. With the rapid growth of asymmetric catalysis, five‐membered heterobiaryl‐based catalysts and ligands have emerged as an efficient complementary toolbox for asymmetric catalysis. Therefore, the development of enantioselective construction of such pentatomic atropisomers has received significant attention in recent decade. Various catalytic asymmetric strategies have been established, including central to axial chirality conversion, direct generation of heteroaryl, direct assembly of aryl‐heteroaryls, functionalization of racemic or prochiral biaryls, and chirality transfer from atropisomeric alkenes. Hundreds of unprecedented pentatomic atropisomers have proliferated. Importantly, a few promising axially chiral catalysts and ligands have been obtained from the prepared heterobiaryls after simple transformations. Hence, recent advances of catalytic asymmetric construction of axially chiral pentatomic heterobiaryls through asymmetric catalysis are summarized in this review, involving their scope, mechanism, transformations, and applications.

Topics & Concepts

AtropisomerEnantioselective synthesisAxial chiralityCatalysisChemistryChirality (physics)Combinatorial chemistryArylStereochemistryOrganic chemistryPhysicsChiral symmetry breakingNambu–Jona-Lasinio modelQuarkQuantum mechanicsAlkylAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis
Recent Advances in Catalytic Atroposelective Construction of Pentatomic Heterobiaryl Scaffolds | Litcius