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3. Synthesis of activated spirocyclopentanes via a cascade Michael/alkylation reaction of ethyl-4-chloro-3-oxobutanoate and 2-arylidene-1,3-indandiones

Author

Nian Hua Luo, Xue Jing Zhang, Ming Yan, and Da Gui Zheng

Subjects
lcsh:QD241-441, chemistry.chemical_compound, Ethyl 4-chloro-3-oxobutanoate, lcsh:Organic chemistry, Chemistry, Cascade, Organic Chemistry, Alkylation, Triethylamine, Medicinal chemistry
Abstract

A cascade Michael/alkylation reaction of ethyl-4-chloro-3-oxobutanoate and 2-Arylidene-1,3indandiones had been studied, providing a number of activated spirocyclopentanes in excellent yields (up to 96%) and diastereoselectivities (up to dr > 20:1). Different bases were evaluated and triethylamine was found to be the most efficient for this transformation under mild reaction.

Published
2015

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