Huck, Fabian and Catti, Lorenzo and Reber, Gian Lino and Tiefenbacher, Konrad. (2022) Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles. Journal of Organic Chemistry, 87 (1). pp. 419-428.
|
PDF
- Accepted Version
722Kb |
Official URL: https://edoc.unibas.ch/91148/
Downloads: Statistics Overview
Abstract
Chiral pyrrolidine derivatives are important building blocks for natural product synthesis. Carbonyl olefin metathesis has recently emerged as a powerful tool for the construction of such building blocks from chiral amino acid derivatives. Here, we demonstrate that the supramolecular resorcinarene catalyst enables access to chiral 2,5-dihydropyrroles under Brønsted acid catalysis. Moreover, this catalytic system even tolerated Lewis-basic-protecting groups like mesylates that are not compatible with alternative catalysts. As expected for conversion inside a closed cavity, the product yield and selectivity depended on the size of the substrates.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Chemie > Synthesis of Functional Modules (Tiefenbacher) |
---|---|
UniBasel Contributors: | Tiefenbacher, Konrad |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | American Chemical Society |
ISSN: | 0022-3263 |
e-ISSN: | 1520-6904 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Language: | English |
Identification Number: |
|
edoc DOI: | |
Last Modified: | 22 Dec 2022 07:25 |
Deposited On: | 15 Dec 2022 07:34 |
Repository Staff Only: item control page