Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The creation of three consecutive chiral carbon centers in one step is achieved using Cu-catalyzed asymmetric silylative cyclization of cyclohexadienone-tethered allenes. Through regioselective β-silylation of the allene and subsequent enantioselective 1,4-addition to cyclohexadienone, this tandem reaction could afford cis-hydrobenzofuran, cis-hydroindole, and cis-hydroindene frameworks with excellent yields (80-98%) and enantioselectivities (94-98% ee) bearing vinylsilane and enone substructures. Meanwhile, this mild transformation is generally compatible with a wide range of functional groups, which allows further conversion of the bicyclic products to bridged and tricyclic ring structures.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201508125 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Catalytic Asymmetric Ionic Hydrogenation of α-Alkyl Styrenes.
J Am Chem Soc
September 2025
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany.
Over the past two decades, chemists have made significant advances in the field of catalytic asymmetric transfer hydrogenation of various unsaturated compounds with biomimetic hydrogen donors. The reduction of carbon-carbon double bonds, however, has been limited to activated substrate classes, such as enals, enones, nitroolefins, or α-(2-hydroxyaryl) styrenes. Here we report a highly enantioselective Brønsted acid-catalyzed ionic hydrogenation of α-alkyl styrenes using a hydrosilane in combination with a protic additive.
View Article and Find Full Text PDFNi-Catalyzed Asymmetric Reductive Addition of Aromatic Iodides to Isatins: A General Access to Chiral 3-Hydroxy-2-Oxindoles.
J Org Chem
August 2025
Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, State Key Laboratory of Power Grid Environmental Protection, Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Engineering Research Center of Organosilicon Compounds & Materia
A nickel-catalyzed enantioselective reductive addition of aryl iodides with isatins has been developed, enabled by a newly designed FOXAP-type ligand bearing a distal bulky silyl group. The reaction proceeds under mild conditions with Mn as the reductant, delivering 3-aryl-3-hydroxyoxindoles in high yields and good to excellent enantioselectivities. This protocol exhibits a broad substrate scope and provides a practical and efficient approach for the synthesis of valuable chiral 3-hydroxy-2-oxindoles bearing a quaternary stereocenter.
View Article and Find Full Text PDFWe report an iridium-catalysed stereoselective cyclisation of aryl alkynes with tethered esters and imides to give silyl-protected ,- and ,-acetals. The optimised conditions afford chiral 5- and 6-membered heterocycles in excellent ee and moderate to high dr and can be isolated chromatographically as single diastereomers. A variety of esters, including acetates, formates, benzoates, and pivalates, can be employed to give functionalised tetrahydrofuran derivatives.
View Article and Find Full Text PDFHFIP-Promoted E-selective Asymmetric Crotylboration of Quaternary α-Silyl Crotylboronate with Aldehydes.
Angew Chem Int Ed Engl
July 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced, Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, C
Polyketide synthesis consistently requires the development of linchpin-type allylboron reagents, such as α-silyl crotylboronates. Traditionally, these reagents feature α-tertiary substitution and are used in aprotic solvents, typically yielding homoallylic alcohols with disubstituted (Z)-vinylsilanes. Here, we report the asymmetric synthesis of enantioenriched quaternary α-silyl crotylboronates via stereospecific allylic Matteson homologation.
View Article and Find Full Text PDFAsymmetric Synthesis of Tetrahydrofurans with Vicinal Stereocenters by Rh/Ru Relay Catalysis.
J Org Chem
May 2025
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
CpRu-catalyzed asymmetric allylic alkylation serves as a versatile synthetic tool but remains underexplored. Herein, we report a relay system combining achiral Rh(OAc) and a chiral pyridine-oxazoline-ligated Cp*Ru catalyst for asymmetric coupling of cinnamyl chlorides with diazo esters, generating silyl enol ethers as key nucleophilic intermediates. This strategy affords chiral tetrahydrofuran derivatives with two vicinal stereocenters.
View Article and Find Full Text PDF