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Synthesis 2022; 54(05): 1422-1430
DOI: 10.1055/a-1672-2260
DOI: 10.1055/a-1672-2260
paper
Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles
This work was supported by Natural Sciences and Engineering Council of Canada (NSERC; Discovery Grant). A.P. acknowledges NSERC for financial support through the PGS-D Scholarship. S.K. acknowledges NSERC for financial support through the CGS-M Scholarship.
Abstract
The present work demonstrates the ability of carboxylic acid tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to decreased yields of ring-opened products, although high regioselectivity for the Type 3 ring-opened products is still maintained. Herein, the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles are reported.
Key words
oxabenzonorbornadiene - cyclopropanated oxabenzonorbornadiene - intramolecular - nucleophilic ring-opening - acid-catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1672-2260.
- Supporting Information
Publication History
Received: 22 September 2021
Accepted after revision: 18 October 2021
Accepted Manuscript online:
18 October 2021
Article published online:
22 November 2021
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