Re‐Evaluation of a Fulvene‐Based Self‐Replicating Diels–Alder Reaction System

We re‐evaluate our claim of a high diastereoselectivity in the self‐relicating Diels–Alder reaction between maleimide 1 and fulvene 3. It was shown that the system has a diastereoselectivity of 1.8:1 for NN‐4:NX‐4, which is contrary to the 16:1 ratio claimed by Dieckmann et al. The analysis of 1H NM...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-07, Vol.26 (41), p.9032-9035
Main Authors: Sevim, İlhan, Pankau, Wolf Matthias, Kiedrowski, Günter
Format: Article
Language:English
Subjects:
Chemistry
Diels-Alder reactions
Diels–Alder reaction
fulvene
NMR
NMR spectroscopy
Nuclear magnetic resonance
Replication
self-replication
Stereoselectivity
supramolecular chemistry
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Summary:We re‐evaluate our claim of a high diastereoselectivity in the self‐relicating Diels–Alder reaction between maleimide 1 and fulvene 3. It was shown that the system has a diastereoselectivity of 1.8:1 for NN‐4:NX‐4, which is contrary to the 16:1 ratio claimed by Dieckmann et al. The analysis of 1H NMR monitoring of the reaction revealed that both replicators show sigmoidal growth which is typical for auto‐catalytic systems. Analytical analysis: The previous claim of high diastereoselectivity for the endo isomers of a self‐replicating Diels–Alder reaction has to be redrawn. We show that the claim is erroneous due to an incorrect assignment of NMR signals. We ask for a re‐evaluation of computational studies that supported the claim (see figure).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201905594