Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

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

doi:10.1039/C5OB02334C

Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

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

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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 language	English
Pages (from-to)	1117-1123
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	3
Early online date	1 Dec 2015
DOIs	https://doi.org/10.1039/C5OB02334C
Publication status	Published - 21 Jan 2016

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10.1039/C5OB02334CLicence: CC BY

Bykova_2015_OBC_Multicomponent_PublishedVersion-CCBY
Copyright 2015 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
Final published version, 1.25 MBLicence: CC BY

Cite this

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title = "Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes",

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.",

author = "Tanya Bykova and Nawaf Al-Maharik and Slawin, {Alexandra Martha Zoya} and David O'Hagan",

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T1 - Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

AU - Bykova, Tanya

AU - Al-Maharik, Nawaf

AU - Slawin, Alexandra Martha Zoya

AU - O'Hagan, David

N1 - The authors thank the EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.

PY - 2016/1/21

Y1 - 2016/1/21

N2 - 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.

AB - 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.

UR - http://www.rsc.org/suppdata/c5/ob/c5ob02334c/c5ob02334c1.pdf

UR - http://www.rsc.org/suppdata/c5/ob/c5ob02334c/c5ob02334c2.cif

U2 - 10.1039/C5OB02334C

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EP - 1123

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 3

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Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes

Abstract

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