Journal ArticleDOI
Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond.
Junxian Yang,Junxian Yang,Ji-Wei Zhang,Wen Bao,Sheng-Qi Qiu,Sheng-Qi Qiu,Shaoyu Li,Shao-Hua Xiang,Jun Song,Junmin Zhang,Bin Tan +10 more
TLDR
In this paper, a chiral phosphoric acid-catalyzed desymmetrization strategy was used to construct axially chiral B-aryl-1,2-azaborines with a C-B stereogenic axis.Abstract:
The previously elusive catalytic enantioselective construction of axially chiral B-aryl-1,2-azaborines with a C-B stereogenic axis has been realized through a chiral phosphoric acid-catalyzed desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the reaction duration could be markedly shortened with weakly acidic N-H in 1,2-azaborine acting as H-bond donor. The scalability of the reaction and facile cleavage of the N-N bond in the product further demonstrated the practicality of this method.read more
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Atropisomers beyond the C–C axial chirality: Advances in catalytic asymmetric synthesis
TL;DR: In this paper , a range of catalytic atroposelective approaches have been reported for the efficient synthesis of X-Y axially chiral skeletons. But, the intrinsic shorter bond length and electron-repelling effect lead to a congested hetero X−Y axis.
Journal ArticleDOI
Organocatalytic Enantioselective Synthesis of Axially Chiral Molecules: Development of Strategies and Skeletons.
TL;DR: In this paper , the intrinsic nucleophilicity of aromatic amines and alcohols was modulated by an electron-withdrawing activating group which could associate with the catalyst for reactivity enhancement and selectivity control.
Journal ArticleDOI
Asymmetric synthesis of N–N axially chiral compounds <i>via</i> organocatalytic atroposelective <i>N</i>-acylation
TL;DR: In this paper , the first atroposelective N-acylation reaction of quinazolinone type benzamides with cinnamic anhydrides was reported.
Journal ArticleDOI
Enantioselective Rh-Catalyzed Azide-Internal-Alkyne Cycloaddition for the Construction of Axially Chiral 1,2,3-Triazoles.
TL;DR: An atroposelective and atom-economical synthesis of axially chiral 1,4,5-trisubstituted 1,2,3-triazoles, directly acting as core chiral units of challenging five-membered atropisomers, via the enantioselectives Rh-catalyzed azide-alkyne cycloaddition (E-RhAAC) of internal alkynes and azides.
Journal ArticleDOI
Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements
TL;DR: An organocatalytic asymmetric construction of hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allene scaffolds bearing both axial chirality and central chircality has been established via a cascade 1,8-addition/dearomatization-cyclization reaction of para-aminophenyl propargylic alcohols with tryptamines in the presence of chiral phosphoric acid (CPA) as mentioned in this paper .
References
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Journal ArticleDOI
Synopsis of some recent tactical application of bioisosteres in drug design.
TL;DR: In this Perspective, some contemporary themes exploring the role of isosteres in drug design are sampled, with an emphasis placed on tactical applications designed to solve the kinds of problems that impinge on compound optimization and the long-term success of drug candidates.
Journal ArticleDOI
New Chiral Phosphorus Ligands for Enantioselective Hydrogenation
Wenjun Tang,Xumu Zhang +1 more
TL;DR: The increasing demand to produce enantiomerically pure pharmaceuticals, agrochemicals, flavors, and other fine chemicals has advanced the field of asymmetric catalytic technologies, and asymmetric hydrogenation utilizing molecular hydrogen to reduce prochiral olefins, ketones, and imines has become one of the most efficient methods for constructing chiral compounds.