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Journal Article

Synthesis of Substituted Tetrahydropyrans via Intermolecular Reactions of δ-Halocarbanions with Aldehydes

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons83836

Brud,  A
Department High-Field Magnetic Resonance, Max Planck Institute for Biological Cybernetics, Max Planck Society;

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Citation

Barbasiewicz, M., Brud, A., & Makosza, M. (2007). Synthesis of Substituted Tetrahydropyrans via Intermolecular Reactions of δ-Halocarbanions with Aldehydes. Synthesis, 2007(8), 1209-1213. doi:10.1055/s-2007-965972.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0013-CE05-9
Abstract
Intramolecular substitution in δ-halocarbanions leading to cyclobutanes is a relatively slow process, thus they readily add to carbonyl groups; the thus-produced anionic adducts cyclize to tetrahydropyran derivatives. A simple mechanistic discussion, optimization of the reaction conditions, and scope of the reaction is presented.