The theoretical-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first experimental report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen- or carbon-acyloxy adducts.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.9b02099 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A chiral pentanidium and pyridinyl-sulphonamide ion pair as an enantioselective organocatalyst for Steglich rearrangement.
Chem Sci
November 2023
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University 21 Nanyang Link Singapore 637371 Republic of Singapore
Enantioselective ion pair catalysis has gained significant attention due to its ability to exert selectivity control in various reactions. Achiral counterions have been found to play crucial roles in modulating reactivity and selectivity. The modular nature of an ion pair catalyst allows rapid alterations of the achiral counterion to achieve optimal outcomes, without the need to modify the more onerous chiral component.
View Article and Find Full Text PDFCatalytic Enantioselective Steglich-Type Rearrangement of Enol Lactones: Asymmetric Synthesis of Spirocyclic 1,3-Diketones.
J Org Chem
November 2022
State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
An example of asymmetric Steglich-type rearrangement of enol lactones is reported. This highly enantioselective acyl transfer reaction is catalyzed by chiral isothiourea at ambient temperature and provides a useful synthetic approach to access enantioenriched spirotricyclic β,β'-diketones from a broad range of indanone or tetralone-derived lactones. Preliminary mechanistic studies suggest the initial formation of an -acylated iminium cation intermediate that induces a following facial selective condensation.
View Article and Find Full Text PDFDesign, Synthesis, and Application of Chiral Bicyclic Imidazole Catalysts.
Acc Chem Res
September 2022
Asymmetric organocatalysis has been considered to be an efficient and reliable strategy for the stereoselective preparation of optically active chemicals. In particular, chiral tertiary amines as Lewis base organocatalysts bearing core structures including quinuclidine, dimethylaminopyridine (DMAP), -methylimidazole (NMI), amidine, etc. have provided new and powerful tools for various chemical transformations.
View Article and Find Full Text PDFBrevifoliol ester induces apoptosis in prostate cancer cells by activation of caspase pathway.
Chem Biol Drug Des
January 2020
CSIR-Central Institute of Medicinal and Aromatics Plants (CSIR-CIMAP), Lucknow, Uttar Pradesh, India.
Prostate cancer is fourth most abundant cancer type around the globe. Brevifoliol, a rearranged taxoid from Taxus walllichiana needles has been derivatized as C5 esters using Steglich esterification reaction. Seventeen diverse analogues were evaluated against a panel of human cancer cell lines by MTT assay.
View Article and Find Full Text PDFQuantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones.
J Org Chem
October 2019
Chemistry Department , Federal University of Juiz de Fora, Campus Martelos , Juiz de Fora , Minas Gerais 36036-900 , Brazil.
The theoretical-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first experimental report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen- or carbon-acyloxy adducts.
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!