Sequential deoxyfluorination approach for the synthesis of protected α,β,γ-trifluoro-δ-amino acids

Raju Cheerlavancha; Aggie Lawer; Marina Cagnes; Mohan Bhadbhade; Luke Hunter

doi:10.1021/ol402756e

Sequential deoxyfluorination approach for the synthesis of protected α,β,γ-trifluoro-δ-amino acids

Org Lett. 2013 Nov 1;15(21):5562-5. doi: 10.1021/ol402756e. Epub 2013 Oct 18.

Authors

Raju Cheerlavancha¹, Aggie Lawer, Marina Cagnes, Mohan Bhadbhade, Luke Hunter

Affiliation

¹ 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.

PMID: 24138127
DOI: 10.1021/ol402756e

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis
Amino Acids / chemistry
Fluorine / chemistry*
Halogenation
Molecular Conformation
Molecular Structure
Stereoisomerism

Substances

Amino Acids
Fluorine