Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion.
density functional theory
macrocycles
rearrangement
ring expansion
ring systems
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Oct 2020
01 Oct 2020
Historique:
received:
01
05
2020
pubmed:
21
5
2020
medline:
9
2
2021
entrez:
21
5
2020
Statut:
ppublish
Résumé
The outcome of ring-expansion reactions based on amino/hydroxyacid side-chain insertion is strongly dependent on ring size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β-ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported by computational results, using a density functional theory (DFT) approach. Calculating the relative Gibbs free energies of the three isomeric species that are formed reversibly during ring expansion enables the viability of new synthetic reactions to be correctly predicted in most cases. The new synthetic and computational results are expected to support the design of new lactam- and β-ketoester-based ring-expansion reactions.
Identifiants
pubmed: 32432817
doi: 10.1002/chem.202002164
pmc: PMC7589337
doi:
Substances chimiques
Amino Acids
0
Hydroxy Acids
0
Lactams
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
12674-12683Subventions
Organisme : Engineering and Physical Sciences Research Council
ID : EP/P029795/1
Organisme : Engineering and Physical Sciences Research Council
ID : EP/H011455/1
Organisme : Engineering and Physical Sciences Research Council
ID : EP/K031589/1
Organisme : Leverhulme Trust
ID : ECF-2015-013
Organisme : Science and Engineering Research Board
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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