Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

6Citations
Citations of this article
9Readers
Mendeley users who have this article in their library.

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, protected as an ether and then a sequence of functional group manipulations carried out to introduce four fluorines. 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. The blocking methyl group renders the ring safe to hydrogen fluoride elimination. 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.

Cite

CITATION STYLE

APA

Bykova, T., Al-Maharik, N., Slawin, A. M. Z., & O’Hagan, D. (2016). Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes. Organic and Biomolecular Chemistry, 14(3), 1117–1123. https://doi.org/10.1039/c5ob02334c

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free