Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

Tanya Bykova, Nawaf Al-Maharik, Alexandra Martha Zoya Slawin, David O'Hagan

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)
1 Downloads (Pure)

Abstract

This paper reports the preparation of methyl substituted all-cis tetrafluorocyclohexanes prepared from a Birch reduction of benzoic acid, worked up with a methyl iodide quench. The resultant methylcyclohexadiene carboxylic acid was reduced to the alcohol and protected. The cyclohexadienyl ring was then epoxidised and the C-O bonds sequentially converted through deoxyfluorination reactions to two sets of isomers of all-cis tetrafluorocyclohexane isomers. Deprotection of the benzylic ether and then oxidation gave aldehydes which were then used in Ugi and Passerini multicomponent reactions, allowing this facially polarised cyclohexane to be incorporated into peptidic structural motifs.

Original languageEnglish
Pages (from-to)1117-1123
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number3
Early online date1 Dec 2015
DOIs
Publication statusPublished - 21 Jan 2016

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