Backbone-homologated amino acids have been synthesized, containing three vicinal fluorine atoms placed stereospecifically along the carbon chain. Different trifluoro stereoisomers are found to have contrasting conformations, consistent with known stereoelectronic effects associated with C-F bonds.
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Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes.
Org Biomol Chem
January 2016
School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
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.
View Article and Find Full Text PDFSequential deoxyfluorination approach for the synthesis of protected α,β,γ-trifluoro-δ-amino acids.
Org Lett
November 2013
School of Chemistry and Mark Wainwright Analytical Centre, The University of New South Wales , Sydney, NSW 2052, Australia , and School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.
Backbone-homologated amino acids have been synthesized, containing three vicinal fluorine atoms placed stereospecifically along the carbon chain. Different trifluoro stereoisomers are found to have contrasting conformations, consistent with known stereoelectronic effects associated with C-F bonds.
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