ArticleAngewandte Chemie (International ed. in English)2022
Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.
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 2 papers.
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Who cites it
2 citing papers in PubMed.
- Potassium Hydroxide as a Cost-Effective Catalyst for Broad-Scope Silylation with TMSCFThe Journal of organic chemistry · 2025Article
- Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
5 authors.
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Abstract
Enantiopure propargylic amines are highly valuable synthetic building blocks. Much effort has been devoted to develop methods for their preparation. The arguably most important strategy is the 1,2-addition of alkynes to imines. Despite remarkable progress, the known methods using Zn and Cu catalysts suffer from the need for high catalyst loadings, typically ranging from 2-60 mol % for neutral aldimine substrates. Here we report a planar chiral Pd complex acting as very efficient catalyst for direct asymmetric alkyne additions to imines, requiring very low catalyst loadings. Turnover numbers of up to 8700 were accomplished. Our investigation suggests that a Pd-acetylide complex is generated as a catalytically relevant intermediate by the aid of an acac ligand acting as internal catalytic base. It is shown that the catalyst is quite stable under the reaction conditions and that product inhibition is not an issue. A total of 39 examples is shown which all yielded almost enantiopure products.
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