Synthesis and Structural Elucidation of IP/I-stereogenic Coumarins

This paper presents the general synthesis of a comprehensive group of P-chiral phosphinyl derivatives with a natural coumarin-type motif. A chiral substituent was attached at the third position of the coumarin molecule via the Knoevenagel procedure using readily available P-chiral phoshinylacetic ac...

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Bibliographic Details
Published in:Symmetry (Basel) 2024-01, Vol.16 (1)
Main Authors: Dziuba, Kamil F, Frynas, Sławomir, Kozioł, Anna E, Szwaczko, Katarzyna
Format: Article
Language:English
Subjects:
Coumarins
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Summary:This paper presents the general synthesis of a comprehensive group of P-chiral phosphinyl derivatives with a natural coumarin-type motif. A chiral substituent was attached at the third position of the coumarin molecule via the Knoevenagel procedure using readily available P-chiral phoshinylacetic acid esters without loss of enantiomeric purity. The application of salicylaldehyde-based derivatives allowed the incorporation of substituents of different electron character into the backbone of these coumarins making them suitable for subsequent chemical modifications. As a result, we gained access to six achiral (2a–g) and a large number ((Sp)-4a–f, (Sp)-6a–e and (Rp)-8a) of new potential chiral ligand precursors, pharmaceuticals, etc. with an imbedded phosphinyl group with evidenced biological activity based on the natural coumarin backbone. The molecular structure, including absolute configuration, was determined for seven compounds.
ISSN:2073-8994
2073-8994
DOI:10.3390/sym16010073