edoc

Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles

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.

[img]
Preview
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