20.500.12556/RUL-144335 Enantioselective organocatalyzed functionalization of tetramic and tetronic acids Organocatalyzed Michael addition of N-substituted tetramic acids to nitroalkene acceptors followed by O-alkylation gave polyfunctionalized tetramic acid (31 examples, 59–94% ee). The enantioselectivity of the product was influenced by the N-substituent of the substrate. Quantum chemical methods provided the mechanistic insights of the studied transformation. The preferred reaction pathway follows the model proposed by Pápai et al. Single crystal structure confirmed the absolute configuration, which was in line with the ECD measured and calculated structure. Additionally, a comparative study of the alkylation of a selected tetramic and tetronic acid with trans-β-nitrostyrene is disclosed. Follow-up amidations demonstrated the applicability of this class of compounds for the incorporation into both dipeptide and depsipeptide sequences. asymmetric organocatalysis bifunctional noncovalent organocatalysts tetramic acids tetronic acids quantum chemical methods amidation dipeptide nekovalentna organokataliza bifunkcionalni nekovalentni organokatalizatorji tetramske kisline tetronske kisline kvantnokemijske metode amidiranje dipeptid true false true Angleški jezik Slovenski jezik Članek v reviji 2023-02-15 09:09:48 2023-02-15 09:09:49 2023-02-16 03:41:14 0000-00-00 00:00:00 2022 0 0 Str. 3840-3855 iss. 22 Vol. 364 22 Nov. 2022 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.7:66.097 1615-4150 10.1002/adsc.202200810 123873283 Adv_Synth_Catal_-_2022_-_Ciber_-_Enantioselective_Org.pdf Adv_Synth_Catal_-_2022_-_Ciber_-_Enantioselective_Org.pdf 1 F8BCBF8D03870F48F2368D72F7501180 7de67e9d4cfd4d71083781bfde2a783cf3c9db0964e049216577d9a4fb4f2a61 22a8bb72-ad2b-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=166615 https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200810 1 c9a298d5-ad07-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=166594 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0