Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones

6-Methylene-5-oxaspiro[2.4]heptanones have been synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds effectively in the presence of the t -BuOK/ t -BuOH/THF catalytic system at room temperature to afford the desired spirocycles in a regio- and s...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-07, Vol.2 (26), p.5325-5333
Main Authors: Samultceva, Sofia O, Dvorko, Marina Yu, Shabalin, Dmitrii A, Ushakov, Igor' A, Vashchenko, Alexander V, Schmidt, Elena Yu, Trofimov, Boris A
Format: Article
Language:English
Subjects:
Chemical synthesis
Dimerization
Ketones
Methylene
Organic compounds
Room temperature
Stereoselectivity
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Summary:6-Methylene-5-oxaspiro[2.4]heptanones have been synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds effectively in the presence of the t -BuOK/ t -BuOH/THF catalytic system at room temperature to afford the desired spirocycles in a regio- and stereoselective manner. A wider synthetic utility of alkynyl cyclopropyl ketones as novel building blocks was demonstrated by the synthesis of diverse spirocyclopropanes. A novel synthetic approach to almost unknown highly functionalized oxa-spirocyclopropanes from alkynyl cyclopropyl ketones is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00854h