Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• acids feature as the most prolific catalytic structure. The last part of the article discusses hydrogen-bond-donating catalysts and other catalyst motifs such as phase-transfer catalysts. Keywords: asymmetric organocatalysis; atropoisomers; atroposelective synthesis; axial chirality; stereogenic axis

• purities (Scheme 3). Sparr and co-workers developed an atroposelective synthesis for tetra-ortho-substituted biaryls 11 by non-canonical polyketide cyclizations [21]. This work was based on an earlier report of the team on the aldol cyclization of naphthyl-substituted unsaturated ketoaldehydes [22]. The

• 24. NHC-catalyzed atroposelective reactions Organocatalysis with N-heterocyclic carbenes (NHC) became one of the main types of covalent activation strategies, which grew into a very diverse area, allowing the synthesis of a wide array of interesting structures. Also, in atroposelective synthesis, NHC

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• will present pioneering examples of chiral phosphoric acid-catalyzed asymmetric syntheses of axially chiral biaryls. In 2013, Kürti and co-workers reported a chiral phosphoric acid-catalyzed aryl–aryl-bond formation process for the regio- and atroposelective synthesis of 2,2′-diamino-1,1

• atroposelective synthesis of axially chiral biarylamino alcohols from the reaction of quinone ester (3) and various 2-naphthylamines 4. In the presence of CPA 2, the axially chiral biarylamino alcohols 5 were obtained in moderate to good yields (up to 85%) and high to excellent enantioselectivities (up to 99% ee

• density functional theory calculations [46]. Recently, Shi, Lin and co-workers reported the atroposelective synthesis of axially chiral biaryls by Pd(II)-catalyzed free amine-directed atroposelective C–H olefination using chiral spirophosphoric acid CPA 5 as an efficient ligand and Ag2CO3 as the oxidant

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

• Hong Yan,
• Zhong-Yi Mao,
• Zhong-Wei Hou,
• Jinshuai Song and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76

• ] have studied the reactions of electrochemically generated NCRs. Particularly, we have recently reported an electrochemical synthesis of imidazo-fused N-heteroaromatic compounds via a radical cyclization cascade [31]. Building on this work, we report herein an atroposelective synthesis of

Recent advances in copper-catalyzed asymmetric coupling reactions

• Fengtao Zhou and
• Qian Cai

Beilstein J. Org. Chem. 2015, 11, 2600–2615, doi:10.3762/bjoc.11.280

• atroposelective synthesis of many very useful axially chiral ligands and biologically important natural products. Some representative examples of these compounds are collected in Scheme 14. In 1997, Andrus et al. [33] used this method for the synthesis of enantiomerically pure bisoxazoline. Lin and Zhong [34

• biaryl compounds. Synthesis of chiral unsymmetrically substituted biaryl compounds. Atroposelective synthesis of biaryl ligands and natural products by using a chiral diether linker. Enantioselective arylation reactions of 2-methylacetoacetates. Asymmetric aryl C–N coupling reactions following a