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Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.
Angew Chem Int Ed Engl
August 2022
Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry, University College Dublin (UCD), Belfield, Dublin 4, Ireland.
We present a facile synthetic route toward a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography.
View Article and Find Full Text PDFZn-Catalyzed enantioselective allylation and allenylation of isatins by virtue of a proline-derived chiral ligand.
Chem Commun (Camb)
February 2022
Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science in University of Science and Technology of China, Hefei, 230026, P. R. China.
An asymmetric allylation and allenylation of isatins with facile organoboron reagents was developed under the catalysis of a Lewis acid. A series of optically pure 3-allyl-3-hydroxyoxindoles and 3-allenyl-3-hydroxyoxindoles can be obtained in excellent yields (up to 99% yield) and high enantioselectivities (up to 97% ee). The possible transition state was supported by DFT calculation and the corresponding mechanism was proposed.
View Article and Find Full Text PDFZn-Catalyzed Diastereo- and Enantioselective Cascade Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles: Stereocontrolled Syntheses of Polycyclic Spirooxindoles.
Org Lett
October 2015
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
A catalytic asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles and 3-nitroindoles has been disclosed with a chiral Zn(OTf)2/diphenylamine-linked bis(oxazoline) complex as the catalyst. A range of enantioenriched polycyclic spirooxindole derivatives containing three contiguous stereocenters were efficiently constructed in quantitative yields with excellent diastereo- and enantioselectivities. Importantly, the metal catalytic strategy in this work is significantly superior to the previous organocatalytic method in the diastereo- and enantioselectivities for almost all of the examined cases.
View Article and Find Full Text PDFZn-catalyzed enantio- and diastereoselective formal [4 + 2] cycloaddition involving two electron-deficient partners: asymmetric synthesis of piperidines from 1-azadienes and nitro-alkenes.
J Am Chem Soc
April 2015
Department of Chemistry, Colorado State University, Ft. Collins, Colorado 80523, United States.
Article Synopsis
- A new method for synthesizing piperidines using a zinc catalyst and a unique BOPA ligand has been developed through a specific [4 + 2] cycloaddition reaction of 1-azadienes and nitro-alkenes, showing high selectivity during the process.
- The modification of ortho substitution on the reacting arenes helps control the reaction environment and lowers the required temperatures, enhancing efficiency.
- Studies suggest that the reaction follows a stepwise mechanism, starting with a Michael-type addition before cyclization, which enables effective reactions even between electron-deficient substrates.
Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis.
Org Lett
June 2013
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
In response to Berkeš's report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berkeš's revised structure.
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