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Enantioselective organocatalyzed functionalization of tetramic and tetronic acids
ID
Ciber, Luka
(
Author
),
ID
Gorenc, Ana
(
Author
),
ID
Hozjan, Mišel
(
Author
),
ID
Požgan, Franc
(
Author
),
ID
Svete, Jurij
(
Author
),
ID
Brodnik, Helena
(
Author
),
ID
Štefane, Bogdan
(
Author
),
ID
Grošelj, Uroš
(
Author
)
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https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200810
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Abstract
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.
Language:
English
Keywords:
asymmetric organocatalysis
,
bifunctional noncovalent organocatalysts
,
tetramic acids
,
tetronic acids
,
quantum chemical methods
,
amidation
,
dipeptide
Work type:
Article
Typology:
1.01 - Original Scientific Article
Organization:
FKKT - Faculty of Chemistry and Chemical Technology
Publication status:
Published
Publication version:
Version of Record
Year:
2022
Number of pages:
Str. 3840-3855
Numbering:
Vol. 364, iss. 22
PID:
20.500.12556/RUL-144335
UDC:
547.7:66.097
ISSN on article:
1615-4150
DOI:
10.1002/adsc.202200810
COBISS.SI-ID:
123873283
Publication date in RUL:
15.02.2023
Views:
620
Downloads:
148
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Record is a part of a journal
Title:
Advanced synthesis & catalysis
Publisher:
Wiley
ISSN:
1615-4150
COBISS.SI-ID:
22726149
Licences
License:
CC BY 4.0, Creative Commons Attribution 4.0 International
Link:
http://creativecommons.org/licenses/by/4.0/
Description:
This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
Secondary language
Language:
Slovenian
Keywords:
nekovalentna organokataliza
,
bifunkcionalni nekovalentni organokatalizatorji
,
tetramske kisline
,
tetronske kisline
,
kvantnokemijske metode
,
amidiranje
,
dipeptid
Projects
Funder:
ARRS - Slovenian Research Agency
Project number:
P1-0179
Name:
Napredna organska sinteza in kataliza
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