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Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions.
In this tutorial review, recent progress in the development of chiral Brønsted acid-catalyzed asymmetric Friedel-Crafts reactions is presented.
Enantioselective intramolecular aza-Michael additions of indoles catalyzed by chiral phosphoric acids.
The asymmetric N-alkylation of indoles proceeds in the absence of electron-withdrawing groups under acidic conditions in order to form Na6(CO3)(SO4), Na2SO4, and Na2CO3 bonds.
Chiral‐Amine‐Catalyzed Asymmetric Bromocyclization of Tryptamine Derivatives
Chiral hexahydropyrro[2,3]indole (HPI) units exist widely in natural and unnatural products with significant biological activities. The enantioselective synthesis of brominated…
Asymmetric construction of polycyclic indoles through olefin cross-metathesis/intramolecular Friedel-Crafts alkylation under sequential catalysis.
Preliminary results on an enantioselective intramolecular Friedel–Crafts alkylation based on sequential catalysis are reported, which was found to be effective with a wide range of substrates.
Ring-closing metathesis/isomerization/Pictet-Spengler cascade via ruthenium/chiral phosphoric acid sequential catalysis.
- Q. Cai, Xiao-Wei Liang, Shou‐Guo Wang, Junwei Zhang, Xiao Zhang, S. You
- ChemistryOrganic letters
- 18 September 2012
Chiral phosphoric acid worked together with Hoveyda-Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-β-carbolines (up to 98% yield, 99% ee) through a ring-closing…
Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines.
Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines has been realized and enantioenriched pyrroleindoline derivatives were obtained in good yields and enantioselectedivity.
Organocatalyzed enantioselective formal [4 + 2] cycloaddition of 2,3-disubstituted indole and methyl vinyl ketone.
This method provides bridged-ring indoline scaffolds containing two quaternary carbon centers with excellent yields and enantioselectivity (up to 98% yield and 98% ee).
Enantioselective Michael/Mannich polycyclization cascade of indolyl enones catalyzed by quinine-derived primary amines.
Both the tricyclic and tetracyclic core of 1 has drawn considerable attention because of its complexity and frequent appearance in natural products and pharmaceuticals and an enantioselective cascade synthesis towards these scaffolds is highly desirable but poses a challenge given.
Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-epi-C and Full Structural Assignment of Trioxacarcin C.
- K. Nicolaou, Q. Cai, Hongbao Sun, Bo-Wen Qin, Shugao Zhu
- ChemistryJournal of the American Chemical Society
- 24 February 2016
The gathered knowledge sets the foundation for the design, synthesis, and biological evalution of analogues of these natural products as potential payloads for antibody-drug conjugates and other delivery systems for targeted and personalized cancer chemotherapy.
Enantioselective Synthesis of Axially Chiral Biaryls by Diels-Alder/Retro-Diels-Alder Reaction of 2-Pyrones with Alkynes.
The enantioselective synthesis of axially chiral biaryls by a copper-catalyzed Diels-Alder/retro-Diels- alder reaction of 2-pyrones with alkynes is reported herein and DFT calculations reveal the reaction mechanism and provide insights into the origins of the stereoselectivities.