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

• of a wide range of axially chiral biaryls, heterobiaryls, vinylarenes, N-arylamines, spiranes, and allenes with high efficiency and excellent stereoselectivity. Keywords: allenes; atropisomerism; axial chirality; chiral phosphoric acid; heterobiaryls; spiranes; Introduction Axial chirality is one

• ] play a crucial role in asymmetric catalysis, the construction of numerous axially chiral biaryls/heterobiaryls [21][35][36][37][38], and other useful asymmetric transformations [5]. Although chiral phosphoric acids have shown promising properties in asymmetric catalysis and play a significant catalytic

• role in the development of axially chiral compounds with biaryls, heterobiaryls, atropisomeric arylalkenes, allenes, and spiranes, there are only few comprehensive reviews in this area. Therefore, the aim of this review is to provide readers with an overview of recent advances in the asymmetric

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

• Xiaochen Du,
• Jianjun Huang,
• Anton A. Nechaev,
• Ruwei Yao,
• Jing Gong,
• Erik V. Van der Eycken,
• Olga P. Pereshivko and
• Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234

• procedures, two asymmetric versions were designed to provide access to axially chiral 2-quinolone-based heterobiaryls such as 2e (Scheme 1c) [45][46]. One substantial drawbacks of the previous methodologies is that they do lack an exploration of the substituent diversity on the nitrogen atom. We decided to

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp²)–H bond arylations

• Fatiha Abdelmalek,
• Fazia Derridj,
• Safia Djebbar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

• ]. In addition, several fluorinated heterobiaryls such as atorvastatin, rosuvastatin, or pitavastatin have been developed as drugs and commercialized by pharmaceutical companies [5]. In both areas, fluorine atoms can modify the properties of organic compounds. It is established that fluorine atoms

Clean and fast cross-coupling of aryl halides in one-pot

• Valerica Pandarus,
• Geneviève Gingras,
• François Béland,
• Rosaria Ciriminna and
• Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

• Affording valued biaryls and heterobiaryls, namely ubiquitous chemical moieties in pharmaceuticals, natural products, photoactive species and many other functional molecules, the Suzuki–Miyaura cross-coupling reaction is widely employed by the fine chemicals and pharmaceutical industries [1]. The reaction

Directed aromatic functionalization

• Victor Snieckus

Beilstein J. Org. Chem. 2011, 7, 1215–1218, doi:10.3762/bjoc.7.141

• sp, sp2, and sp3, and –O, –N, and –S bonds are made to the aromatic ring carbon [25]. These strategies rapidly furnish biaryls/heterobiaryls, and condensed complex aromatics/heteroaromatics whose construction by previous generation methods (e.g., diazonium and radical coupling) has been clearly

Cationic gold(I) axially chiral biaryl bisphosphine complex-catalyzed atropselective synthesis of heterobiaryls

• Tetsuro Shibuya,
• Kyosuke Nakamura and
• Ken Tanaka

Beilstein J. Org. Chem. 2011, 7, 944–950, doi:10.3762/bjoc.7.105

• complex catalyzes the atropselective intramolecular hydroarylation of alkynes leading to enantioenriched axially chiral 4-aryl-2-quinolinones and 4-arylcoumarins with up to 61% ee. Keywords: asymmetric catalysis; axial chirality; gold; heterobiaryls; hydroarylation; Introduction Atropselective biaryl

• bisphosphine ligands for the cationic gold(I)-complex catalyzed atropselective intramolecular hydroarylation of 1a.a Cationic gold(I)-complex catalyzed atropselective intramolecular hydroarylation of 1a–g leading to heterobiaryls 2a–g.a Supporting Information Supporting Information File 62: 1H and 13C NMR