Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 42, Pages 16711-16713Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja207322d
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Funding
- Japanese Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science
- Grants-in-Aid for Scientific Research [21106001, 10J04974, 23350017, 21106005] Funding Source: KAKEN
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Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalytic cycloetherification of epsilon-hydroxy-alpha,beta-unsaturated ketones mediated by cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.
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