Allylic-Allylic Alkylation with 3,5-Dimethyl-4-nitroisoxazole: A Route to Dicarboxylic Acid Derivatives
Authors:
- Dorota Kowalczyk-Dworak,
- Marcin Grzegorz Kwit,
- Łukasz Albrecht
Abstract
In this work, the first application of 3,5-dimethyl-4-nitroisoxazole as a vinylogous pronucleophile in the allylic-allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been realized under nucleophilic catalysis conditions with dimeric cinchona alkaloids, providing excellent enantiocontrol of the process. The usefulness of the products thus obtained has been confirmed in selected chemoselective reactions. The most important one involves the transformation of the isoxazole moiety into a carboxylic acid group, thus opening access to dicarboxylic acid derivatives. © 2020 American Chemical Society.
- Record ID
- UAMc1bd2b66f7e04c95b308177d3ab1050e
- Author
- Journal series
- Journal of Organic Chemistry, ISSN 0022-3263, e-ISSN 1520-6904
- Issue year
- 2020
- Vol
- 85
- No
- 5
- Pages
- 2938-2944
- ASJC Classification
- DOI
- DOI:10.1021/acs.joc.9b02530 Opening in a new tab
- URL
- https://pubs.acs.org/doi/10.1021/acs.joc.9b02530 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 140
- Score source
- journalList
- Score
- = 140.0, 15-02-2022, ArticleFromJournal
- Publication indicators
- = 6; : 2018 = 0.952; : 2019 (2 years) = 4.335 - 2019 (5 years) =4.072
Share
- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAMc1bd2b66f7e04c95b308177d3ab1050e/
- URN
urn:amu-prod:UAMc1bd2b66f7e04c95b308177d3ab1050e
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.