A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes highlighting two vinylogous steps, an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction triggering a formal (4+2) cycloaddition. This work opens a new route towards bio-relevant and original tricyclic thiochroman derivatives.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.202301311 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Organocatalytic Enantioselective Friedel-Crafts Reaction of Phenanthrenequinones and Indoles.
Molecules
January 2025
Department of Pharmacy, Jilin Medical University, Jilin 132013, China.
An efficient stereoselective synthesis of 10-hydroxy-10-(1-indol-3-yl)-9-(10)-phenanthrene derivatives was realized through an organocatalyzed Friedel-Crafts reaction of phenanthrenequinones and indoles using a (,)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73-90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay.
View Article and Find Full Text PDFIn-Cage Recombination Facilitates the Enantioselective Organocatalytic [1,2]-Rearrangement of Allylic Ammonium Ylides.
J Am Chem Soc
January 2025
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St. Andrews, KY16 9ST, U.K.
The [1,2]-rearrangement of allylic ammonium ylides is traditionally observed as a competitive minor pathway alongside the thermally allowed [2,3]-sigmatropic rearrangement. Concerted [1,2]-rearrangements are formally forbidden, with these processes believed to proceed through homolytic C-N bond fission of the ylide, followed by radical-radical recombination. The challenges associated with developing a catalytic enantioselective [1,2]-rearrangement of allylic ammonium ylides therefore lie in biasing the reaction pathway to favor the [1,2]-reaction product, alongside controlling a stereoselective radical-radical recombination event.
View Article and Find Full Text PDFOrganocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam ,-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic -Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones.
J Org Chem
December 2024
Henan Key Laboratory of Natural Medicine Innovation and Transformation, State Key Laboratory of Antiviral Drugs, Henan University, Kaifeng, Henan 475004, P. R. China.
A highly stereoselective protocol for the (3 + 2)-annulation of biphenyl-bridged seven-membered cyclic -sulfonylimines with γ-hydroxy-α,β-unsaturated ketones was developed. The reactions afforded a wide range of chiral [5.7]-fused ε-sultams bearing N-adjacent 1,3-stereocenters in excellent yields (93-98% yields) and high enantio/diastereoselectivities (up to >99% ee, >20:1 d.
View Article and Find Full Text PDFSynthesis of P(V)-Stereogenic Phosphorus Compounds via Organocatalytic Asymmetric Condensation.
J Am Chem Soc
December 2024
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
Enantioenriched phosphorus(V)-stereogenic compounds, featuring a pentavalent phosphorus atom as the stereogenic center, are crucial in various natural products, drugs, bioactive molecules, and catalysts/ligands. While a handful of stereoselective synthetic approaches have been developed, achieving direct stereocontrol at the phosphorus atom through catalytic generation of phosphorus(V)-heteroatom bonds continues to be a formidable challenge. Here, we disclose an organocatalytic asymmetric condensation strategy that employs a novel activation mode of stable feedstock phosphinic acids by the formation of mixed phosphinic anhydride as the reactive species to facilitate further catalyst-controlled asymmetric P-O bond formations, involving a dynamic kinetic asymmetric transformation (DYKAT) process with alcohol nucleophiles via a cinchonidine-derived bifunctional catalyst.
View Article and Find Full Text PDFStereoselective Radical Acylfluoroalkylation of Bicyclobutanes via N-Heterocyclic Carbene Catalysis.
Angew Chem Int Ed Engl
November 2024
School of Chemistry, Dalian University of Technology, Dalian, 116024, China.
Cyclobutanes are prominent structural components in natural products and drug molecules. With the advent of strain-release-driven synthesis, ring-opening reactions of bicyclo[1.1.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!