Asymmetric Synthesis of Atropisomeric Compounds with an N‒C Chiral Axis

Organocatalyzed Asymmetric Synthesis of Axially, Planar, and Helical Chiral Compounds

“…Axiallyc hiral anilides have received much attention in recent years as attractive atropisomeric compounds possessing an NÀ Ar chiral axis. [2] Interesting properties and utility of axially chiral anilides have been found not only in the research field of organic chemistry but also in biological chemistry,a nd actually Scheme11. Asymmetric desymmetrization of diaminobiarylc ompound under phase-transferc onditions.…”

“…The importance of axially, [1][2][3] planar, [4] and helical [5] chiral compounds has widely been recognized in both academic and industrial chemical communities. Aw ide variety of chiral ligands and catalysts have been designed based on these chiral scaffolds ( Figure 1), and these chirall igandsa nd catalysts were utilized for various types of asymmetrict ransformationst op roduce important chiral compounds in optically enriched form.…”

“…Amongt he enantioselective preparation of these chiral compounds,c atalytic asymmetric approaches are one of the most efficient and modern approaches in organic synthesis. [6] Althoughs everale fficient metal-catalyzed approaches have been reported, [1][2][3][4][5] the further development of efficient approaches for catalytic asymmetric synthesis of these chiral compounds is highly desirable due to the high synthetic utility of these chiral compounds. In this situation, organocatalyzeda pproaches, which are one of the most reliable catalytic asymmetric methods nowadays, [9] became ah ot topic especially in the last few years.…”

The synthesis of optically active N–C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor

“…Various N--C axially chiral compounds have been prepared with high enantioselectivity through catalytic asymmetric reactions, and used as chiral building blocks and chiral ligands. 2,3 In addition, N--C axially chiral compounds have been found useful not only in the field of synthetic organic chemistry but also in molecular devices (molecular rotors). 4 Molecular rotors, whose rate of rotation around a bond can be controlled by external stimuli, are one of the most common classes of molecular devices.…”

“…2,3 These compounds have an amide skeleton like anilides, imides, lactams and urea, or a nitrogen--containing aromatic heterocyclic framework like indole and 4--quinolinone, but there has been no report on the catalytic enantioselctive synthesis of simple N--C axially chiral amine. Only three reports have appeared on the preparation of optically active axially chiral amines by optical resolution.…”