Journal
ORGANIC LETTERS
Volume 16, Issue 23, Pages 6264-6266Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503104b
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Funding
- Japanese Ministry of Education, Culture, Sports, Science and Technology
- Grants-in-Aid for Scientific Research [25888012] Funding Source: KAKEN
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Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to gamma-hydroxy-alpha,beta-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into beta-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of alpha,beta-unsaturated carbonyl compounds.
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