ArticleAngewandte Chemie (International ed. in English)2019
Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 61 citations in OpenAlex.
- Copper-catalyzed direct regioselective C5-H alkylation reactions of functionalized indoles with α-diazomalonates.Chemical science · 2025Article
- Enantioselective Synthesis of 2,3-Disubstituted Azetidines via Copper-Catalyzed Boryl Allylation of Azetines.Journal of the American Chemical Society · 2025Article
- New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks.Organic & biomolecular chemistry · 2022Review
- Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.Molecules (Basel, Switzerland) · 2022Review
- Azetidine synthesis enabled by photo-induced copper catalysis via [3+1] radical cascade cyclization.Innovation (Cambridge (Mass.)) · 2022Article
- Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.Journal of the American Chemical Society · 2022Article
- Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
The all-cis stereoisomers of tetrasubstituted azetidine-2-carboxylic acids and derivatives that possess three chiral centers have been prepared in high yield and stereocontrol from silyl-protected Z-γ-substituted enoldiazoacetates and imido-sulfur ylides by asymmetric [3+1]-cycloaddition using chiral sabox copper(I) catalysis followed by Pd/C catalytic hydrogenation. Hydrogenation of the chiral p-methoxybenzyl azetine-2-carboxylates occurs with both hydrogen addition to the C=C bond and hydrogenolysis of the ester.
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