ArticleCommunications chemistry2020
N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation.
Article in Communications chemistry, 2020. 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.
- Carbon and Heteroatom Activation via N-Heterocyclic Carbene-Bound Dearomative Intermediates for Stereoselective Annulation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Dynamic kinetic resolution of γ,γ-disubstituted indole 2-carboxaldehydesChemical science · 2022Article
- Asymmetric higher-order [10 +Chemical science · 2022Article
- Biomimetic enantioselective synthesis of β,β-difluoro-α-amino acid derivatives.Communications chemistry · 2021Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Higher-order cycloadditions are a powerful strategy for the construction of polycycles in one step. However, an efficient and concise version for the induction of asymmetry is lacking. N-heterocyclic carbenes are widely used organocatalysts for asymmetric synthesis and could be an ideal choice for enantioselective higher-order cycloadditions. Here, we report an enantioselective [10 + 2] annulation between catalytically formed aza-benzofulvene intermediates and trifluoromethyl ketone derivatives. This protocol exhibits a wide scope, high yields, and good ee values, reflecting a robust and efficient higher-order cycloaddition. Density functional theory calculations provide an accurate prediction of the reaction enantioselectivity, and in-depth insight to the origins of stereocontrol.
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Registered trials
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