A General Method for the Preparation of 7-Substituted Cyclohexenals and Cycloheptenals

Todd K. Jones, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

A general procedure for the preparation of γ-substituted or β'-unsaturated cycloalkenals is described. Starting from 2-cycloalkenones substituents may be introduced as nucleophiles by 1,4-addition followed by trapping of the regiospecifically generated enolate (86-92%). Peracid oxidation of the enol silane derivative produces an a-hydroxy ketone which, after protection (70-93%), is homologated to an enol ether by a Horner-Wittig reaction. Mild hydrolysis of the labile vinylogous acetal produces the aldehydes in good yields (62-75%), Advantages of this method in comparison to known procedures are discussed as are other unsuccessful approaches to this substitution pattern.

Original languageEnglish (US)
Pages (from-to)4037-4045
Number of pages9
JournalJournal of Organic Chemistry
Volume50
Issue number21
DOIs
StatePublished - Oct 1985

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Silanes
Acetals
Nucleophiles
Ketones
Aldehydes
Ether
Hydrolysis
Substitution reactions
Derivatives
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A General Method for the Preparation of 7-Substituted Cyclohexenals and Cycloheptenals. / Jones, Todd K.; Denmark, Scott E.

In: Journal of Organic Chemistry, Vol. 50, No. 21, 10.1985, p. 4037-4045.

Research output: Contribution to journalArticle

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