Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/cc050098j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Late-Stage Pd(II)-Catalyzed C(sp3)-H Functionalization of Peptides Directed by a Removable, Backbone-Inserted Amidoxime Ether.
Angew Chem Int Ed Engl
January 2025
University of Melbourne, School of Chemistry, 30 Flemington Rd., VIC 3095, Parkville, AUSTRALIA.
Palladium(II)-catalyzed C-H functionalization has attracted considerable attention as a pathway to late-stage modification of peptides. Herein, we report the Pd-catalyzed C(sp3)-H arylation of peptides directed by an amidoxime ether, which can be easily incorporated into peptides at any amide bond. Site- and stereoselective arylation of peptides has been achieved, including an unprecedented example of C-H arylation of an internal residue.
View Article and Find Full Text PDFCatalytic (4+2) Annulation via Regio- and Enantioselective Interception of in-situ Generated Alkylgold Intermediate.
Angew Chem Int Ed Engl
July 2024
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. China.
A regio- and stereoselective stepwise (4+2) annulation of N-propargylamides and α,β-unsaturated imines/ketones has been accomplished with synergetic catalysis by a combination of a gold-complex and a chiral quinine-derived squaramide (QN-SQA), leading to highly functionalized chiral tetrahydropyridines/dihydropyrans in good to high yields with generally excellent enantioselectivity. Mechanistic studies and DFT calculations indicate that the in situ formed alkylgold species is the key intermediate in this transformation, and the amide group served as a traceless directing group in this highly selective transformation. This method complements the enantioselective (4+2) annulation of allene reagents, providing the formal internal C-C π-bond cycloaddition products, which is challenging and remains elusive.
View Article and Find Full Text PDFAn Asymmetric Hydrogenation/N-Alkylation Sequence for a Step-Economical Route to Indolizidines and Quinolizidines.
Angew Chem Int Ed Engl
October 2023
College of Chemistry and Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100, P. R. China.
The direct catalytic asymmetric hydrogenation of pyridines for the synthesis of piperidines remains a challenge. Herein, we report a one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Brønsted acid activation strategy. Catalyzed by an iridium-BINAP complex, the substrates undergo ketone reduction, cyclization and pyridine hydrogenation in sequence to form indolizidines and quinolizidines.
View Article and Find Full Text PDFAtroposelective Arene-Forming Alkene Metathesis.
Angew Chem Int Ed Engl
December 2022
Department of Chemistry, University of Basel, Johanns-Ring 19, 4056, Basel, Switzerland.
Alkene metathesis catalyzed by enantiopure metal alkylidene complexes enables exceptionally versatile strategies to products with configurationally-defined stereocenters. Desymmetrization processes thereby provide reliable stereoselective routes to aliphatic structures, while the differentiation of aromatic stereogenic units remained an outstanding challenge. Herein, we describe the feasibility of alkene metathesis to catalytically control stereogenic axes by traceless arene formation.
View Article and Find Full Text PDFSynthesis of Diverse γ-Lactams via Rh-Catalyzed C(sp)-H Addition to Aliphatic Nitriles.
Org Lett
July 2022
College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China.
We herein report an unprecedented pathway to access γ-lactams using acetonitrile analogues as coupling partners without oxidants, ligands, and Lewis acids. The reaction undergoes Rh-catalyzed C(sp)-H addition to carbon-bound nitriles with the aid of an amide traceless auxiliary followed by an annulation sequence, featuring a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations highlight the potential synthetic utility of this methodology.
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!