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Synthesis 2019; 51(04): 899-906
DOI: 10.1055/s-0037-1609637
DOI: 10.1055/s-0037-1609637
paper
Diastereoselective Synthesis of Spirobarbiturate-Cyclopropanes through Organobase-Mediated Spirocyclopropanation of Barbiturate-Based Olefins with Benzyl Chlorides
We are grateful to the NSFC (#21302173) and Henan Department of Education (#19A150049) for financial support.Further Information
Publication History
Received: 13 September 2018
Accepted after revision: 10 October 2018
Publication Date:
06 November 2018 (online)
Abstract
The organobase-mediated diastereoselective spirocyclopropanation of barbiturate-based olefins with 2,4-disubstituted benzyl chlorides has been developed. The reactions were carried out efficiently to afford the desired spirobarbiturate-cyclopropanes in up to 95% yield with more than 20:1 dr in favor of anti-isomers. In order to extend synthetic utility of the spiro-products, a Lewis acid induced cyclopropane-ring-expansion isomerization was also demonstrated.
Key words
spirobarbiturate-cyclopropane - spirocyclopropanation - barbiturate-based olefin - benzyl chloride - diastereoselective - synthetic methodology - organobaseSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609637.
- Supporting Information
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- 12a We could not obtain the single-step Michael addition product, which was the protonated form of the intermediate A or B in Scheme 3. The spirobarbiturate-cyclopropanes were the only separable products under various basic conditions in this study.
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