Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls
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The first chiral phosphoric acid (CPA) catalyzed cycloaddition-elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing the highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities as mentioned in this paper.Abstract:
The first chiral phosphoric acid (CPA) catalyzed cycloaddition-elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing the highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities. The success of this strategy derives from stepwise process involving CPA-catalyzed asymmetric formal [3+2] cycloaddition and subsequent central-to-axial chirality conversion by elimination of a carbamate. In addition, the practicality of this reaction had been verified by varieties of transformations towards functionalized atropisomers.read more
Citations
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Organocatalytic Atroposelective Synthesis of Indole Derivatives Bearing Axial Chirality: Strategies and Applications.
Hong-Hao Zhang,Feng Shi +1 more
TL;DR: In this article , the authors proposed a method for the atropisomeric indole derivatives with axial chirality to synthesize enantioselective transformations of platform molecules.
Journal ArticleDOI
Organocatalytic Atroposelective Synthesis of N-N Axially Chiral Indoles and Pyrroles by De Novo Ring Formation.
TL;DR: In this article , the first highly atroposelective construction of N-N axially chiral indole scaffolds were established via a new strategy of de novo ring formation, which makes use of the organocatalytic asymmetric Paal-Knorr reaction of well-designed N-aminoindoles with 1,4-diketones, thus affording high yields for N-pyrrolylindoles.
Journal ArticleDOI
Catalytic Asymmetric Synthesis of Axially Chiral 3,3'‐Bisindoles by Direct Coupling of Indole Rings
TL;DR: In this article , a new enantioselective synthesis strategy for axially chiral 3,3'-bisindoles was devised by the direct coupling of two indole rings.
Journal ArticleDOI
Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls
TL;DR: In this article , a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes is described, and axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands.
Journal ArticleDOI
Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls
TL;DR: In this article , a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes is described, and axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands.
References
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