ArticleAngewandte Chemie (International ed. in English)2022
Enantioselective (8+3) Cycloadditions by Activation of Donor-Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Cycloaddition and functionalization reactions involving tropone.RSC advances · 2025Review
- Thiazolylcyanocyclopropanes: Novel Donor-Acceptor Cyclopropanes for Accessing Thiazole-Containing Targets.Molecules (Basel, Switzerland) · 2025Article
- Quantum Chemical Study of the Cycloaddition Reaction of Tropone with 1,1-Diethoxyethene Catalyzed by B(CACS omega · 2023Article
- Enantioselective (8+3) Cycloadditions by Activation of Donor-Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
6 authors.
Funding
Abstract
A novel enantioselective (8+3) cycloaddition between donor-acceptor cyclopropanes and heptafulvenoids catalysed by a chiral bifunctional Brønsted base is described. Importantly, the reaction, which leverages an anionic activation strategy, is divergent from prototypical Lewis-acid activation protocols. A series of cyclopropylketones react with tropones affording the desired (8+3) cycloadducts in high yield and enantiomeric excess. For barbiturate substituted heptafulvenes, the (8+3) cycloaddition with cyclopropylketones proceeds in good yield, excellent diastereoselectivity and high enantiomeric excess. The experimental work is supported by DFT calculations, which indicate that the bifunctional organocatalyst activates both the donor-acceptor cyclopropane and tropone; the reaction proceeds in a step-wise manner with the ring-closure being the stereodetermining step.
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