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First access to the spin-labelled β-amino acid POAC in an enantiopure state by resolution through its binaphthyl esters |
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| Authors: | Karen Wright,Fernando FormaggioClaudio Toniolo,Roland Tö rö kAntal Pé ter,Michel WakselmanJean-Paul Mazaleyrat |
| Affiliation: | a SIRCOB, UMR CNRS 8086, Bât. Lavoisier, University of Versailles, F-78000 Versailles, France b Institute of Biomolecular Chemistry, CNR, Department of Organic Chemistry, University of Padova, I-35131 Padova, Italy c Department of Inorganic and Analytical Chemistry, University of Szeged, PO Box 440, H-6701 Szeged, Hungary |
| Abstract: | Resolution of trans 3-(9-fluorenylmethyloxycarbonylamino)-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (Fmoc-POAC-OH) was quickly achieved upon esterification with (aR)-1,1′-binaphthyl-2,2′-diol, chromatographic separation of the obtained diastereomers, and facile saponification of the aryl ester function with removal of the chiral auxiliary. |
| Keywords: | binaphthol esters chiral nitroxides modified β-amino acids spin-labelled amino acids POAC resolution |
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