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Synthesis 2021; 53(04): 731-753
DOI: 10.1055/s-0040-1706547
DOI: 10.1055/s-0040-1706547
paper
Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes
This work was supported by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) and Japan Society for the Promotion of Science (JSPS) (KAKENHI Grant Number JP26410048).
Abstract
Inter- and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl4 or SnBr4 stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.
Key words
cyclobutane - ethenetricarboxylate - styrene - intermolecular cycloaddition - intramolecular cycloadditionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706547.
- Supporting Information
Publication History
Received: 25 August 2020
Accepted after revision: 24 September 2020
Article published online:
02 November 2020
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