Journal
ORGANIC LETTERS
Volume 7, Issue 15, Pages 3167-3170Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol050715c
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- NIGMS NIH HHS [GM-49093] Funding Source: Medline
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A series of quinone monoacetals bearing electron-withdrawing groups was treated with diethyl malonate and other bifunctional nucleophiles in the presence of KO-t-Bu in THF. Reactions of ethyl 3-nitroproplonate or diethyl malonate resulted in single conjugate addition adducts. When ethyl acetoacetate was used as a nucleophile, bridged bicyclic products were obtained in good yields. The regiochemistry of conjugate addition was dependent on the quinone monoacetal substitution.
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