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Issue 40, 2020
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Diastereoselective synthesis and conformational analysis of 4,5-difluoropipecolic acids

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Abstract

Stereoselectively-fluorinated analogs of pipecolic acid have been investigated through a combined theoretical and experimental approach. Three of the four possible diastereoisomers of 4,5-difluoropipecolic acid were successfully synthesized via deoxyfluorination chemistry, navigating a complex reaction network that included neighboring group participation, rearrangement, and elimination pathways. A DFT-based conformational study, supported by NMR J-based analysis, revealed that the different diastereoisomers of 4,5-difluoropipecolic acid preferentially adopt different puckers of the six-membered ring. These findings could have future relevance for the conformational control of biologically active peptides.

Graphical abstract: Diastereoselective synthesis and conformational analysis of 4,5-difluoropipecolic acids

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Supplementary files

Article information


Submitted
02 Sep 2020
Accepted
28 Sep 2020
First published
01 Oct 2020

Org. Biomol. Chem., 2020,18, 8192-8198
Article type
Paper

Diastereoselective synthesis and conformational analysis of 4,5-difluoropipecolic acids

S. Chen, Y. Ruan, J. Lu, L. Hunter and X. Hu, Org. Biomol. Chem., 2020, 18, 8192
DOI: 10.1039/D0OB01811B

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