ArticleNature communications2020
Copper(I)-catalyzed asymmetric 1,6-conjugate allylation.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 31 citations in OpenAlex.
- Ring-Expanded N-Heterocyclic Carbene (reNHC) Complexes: Applications in Transition Metal Catalysis.Coordination chemistry reviews · 2024Article
- Chiral π-Cu(ii)-catalyzed site-,Chemical science · 2024Article
- Chiral oxazolidines acting as transient hydroxyalkyl-functionalized N-heterocyclic carbenes: an efficient route to air stable copper and gold complexes for asymmetric catalysis.Chemical science · 2022Article
- Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes.Nature communications · 2022Article
- Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals.Angewandte Chemie (International ed. in English) · 2021Article
- Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Catalytic asymmetric conjugate allylation of unsaturated carbonyl compounds is usually difficult to achieve, as 1,2-addition proceeds dominantly and high asymmetric induction is a challenging task. Herein, we disclose a copper(I)-NHC complex catalyzed asymmetric 1,6-conjugate allylation of 2,2-dimethyl-6-alkenyl-4H-1,3-dioxin-4-ones. The phenolic hydroxyl group in NHC ligands is found to be pivotal to obtain the desired products. Both aryl group and alkyl group at δ-position are well tolerated with the corresponding products generated in moderate to high yields and high enantioselectivity. Moreover, both 2-substituted and 3-substituted allylboronates serve as acceptable allylation reagents. At last, the synthetic utility of the products is demonstrated in several transformations by means of the versatile terminal olefin and dioxinone groups.
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Registered trials
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