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A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols.
Nat Commun
January 2025
The Institute for Advanced Studies and Hongyi Honor College, Wuhan University, Wuhan, China.
Optically pure 1,2-diols and 1,3-diols are the most privileged structural motifs, widely present in natural products, pharmaceuticals and chiral auxiliaries or ligands. However, their synthesis relies on the use of toxic or expensive metal catalysts or suffer from low regioselectivity. Catalytic asymmetric synthesis of optically pure 1,n-diols from bulk chemicals in a highly stereoselective and atom-economical manner remains a formidable challenge.
View Article and Find Full Text PDFHighly Diastereoselective Access to Densely Functionalized Piperidine Cores of Influenza Endonuclease Inhibitors via a Metal-Free S1 Approach.
J Org Chem
January 2025
Evotec (US) Inc., 303B College Road East, Princeton, New Jersey 08540, United States.
A novel, highly diastereoselective, and metal-free synthesis of multisubstituted piperidines via an S1 approach is reported in this study. The method allows for the preparation of highly functionalized compounds with exceptional diastereomeric selectivities and consistently reproducible yields. These compounds are of significant interest due to their remarkable biological activities toward influenza endonuclease.
View Article and Find Full Text PDFSulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability.
Sci Rep
December 2024
Department of Organic and Polymer Chemistry, Faculty of Chemistry, Kharazmi University, Tehran, 15719-14911, Iran.
This study investigates the repurposing of asphaltene, a petroleum waste product, as a catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated for its efficacy in catalyzing the Mannich reaction, displaying notable diastereoselectivity and operating effectively under mild conditions. Characterization of the catalyst's chemical composition, structure, and thermal stability was conducted using FT-IR, TGA, XRD, CHN, BET-BJH, SEM, and EDS analyses.
View Article and Find Full Text PDFAsymmetric desymmetrization of 2,5-cyclohexadienones initiated by organocatalytic conjugate addition to 4-nitro-5-styrylisoxazoles.
Chem Commun (Camb)
December 2024
Department of Chemistry, Indian Institute of Technology Jammu, Jagti, NH-44, Nagrota Bypass, Jammu 181221, J&K, India.
A highly regio-, enantio- and diastereo-selective strategy involving initial enantioselective conjugate addition to 4-nitro-5-styrylisoxazoles serves as a key step for the desymmetrization of 2,5-cyclohexadienones has been disclosed. We have designed a new class of 2,5-cyclohexadienones appended with 4-nitro-5-styrylisoxazoles to undergo organocatalytic asymmetric double or triple conjugate addition in a domino sequence depending on the substrate type leading to desymmetrization of the 2,5-cyclohexadienone core. The developed protocol allows the construction of a valuable hydrophenanthrene core or a unique bridged scaffold bearing multiple chiral centers with excellent enantio- (up to >99.
View Article and Find Full Text PDFHighly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and Generated Pyridinium Ylide.
J Org Chem
December 2024
Department of Chemistry, Indian Institute of Technology Jodhpur, Rajasthan 342030, India.
We report a cascade approach for the synthesis of 2,3-dihydropyrroles derivatives via a formal [4 + 1] annulation reaction of α,β-unsaturated imines with generated pyridinium ylides. Importantly, this protocol is compatible with diverse substituted imines as well as pyridinium ylides, constructing 2,3-dihydropyrroles with excellent yield and selectivity. Thereafter, the Merrifield resin-supported pyridinium ylide as a potential C1 synthon was also employed in our strategy and reused several times, resulting in products with excellent yield and diastereoselectivity.
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