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.
Citation
Bykova , T , Al-Maharik , N , Slawin , A M Z & O'Hagan , D 2016 , ' Multicomponent reactions of methyl substituted all- cis tetrafluorocyclohexane aldehydes ' , Organic & Biomolecular Chemistry , vol. 14 , no. 3 , pp. 1117-1123 . https://doi.org/10.1039/C5OB02334C
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
ISSN
1477-0520Type
Journal article
Rights
Copyright 2015 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
Description
The authors thank the EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.Collections
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