Journal
ORGANIC LETTERS
Volume 13, Issue 21, Pages 5758-5761Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol202331j
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- National Science Council, Taiwan, ROC
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Asymmetric domino Michael acetalization reactions of 2-hydroxynitrostyrene and 2-oxocyclohexanecarbaldehyde with a bifunctional thioureatertiary-amine organocatalyst, e.g., the Takemoto catalyst, followed by oxidation providing the 1',3-spiro-2'-oxocyclohexan-3,4-dihydrocoumarin having one all-carbon quaternary stereocenter with excellent diastereo- and enantioselectivities (up to >99% ee), are described. The structures and absolute configurations of the products were confirmed by X-ray analysis.
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