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Chemoselective,Substrate‐directed Fluorination of Functionalized Cyclopentane β‐Amino Acids |
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| Authors: | Dr Loránd Kiss Dr Melinda Nonn Prof Reijo Sillanpää Prof Matti Haukka Prof Santos Fustero Prof Ferenc Fülöp |
| Institution: | 1. Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary;2. MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged, Hungary;3. Department of Chemistry, University of Jyv?skyl?, Jyv?skyl?, Finland;4. Universidad de Valencia, Facultad de Farmàcia, Departamento de Química Orgánica, Valencia, Spain |
| Abstract: | This work describes a substrate‐directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH2F or CHF2 moieties in their structure have been synthesized from diexo‐ or diendo‐norbornene β‐amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon–carbon double bond of the norbornene β‐amino acids, followed by transformation of the resulted ?all cis“ and ?trans“ diformyl intermediates by fluorination with ?chemodifferentiation“. |
| Keywords: | amino acids cyclization fluorine molecular diversity substituent effects |