ArticleAngewandte Chemie (International ed. in English)2023
In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Advances in Flow Chemistry for Organolithium-Based Synthesis: A Process Perspective.Molecules (Basel, Switzerland) · 2025Review
- Stereospecific cross-coupling reactions: Programmed assembly of chiral molecules by reaction of chiral reagents.Science advances · 2025Review
- Synthetic Process Development of (Organic process research & development · 2024Article
- Calculation-assisted regioselective functionalization of the imidazo[1,2-Chemical science · 2023Article
- In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
7 authors.
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Abstract
We report a practical in situ quench (ISQ) procedure involving the generation of chiral secondary alkyllithiums from secondary alkyl iodides (including functionalized iodides bearing an ester or a nitrile) in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, isocyanates, sulfides, or boronates. This ISQ-reaction allowed the preparation of a broad range of optically enriched ketones, alcohols, amides, sulfides and boronic acid esters in typically 90-98 % ee. Remarkably, these reactions were performed at -78 °C or -40 °C in batch. A continuous flow set-up permitted reaction temperatures between -20 °C and 0 °C and allowed a scale-up up to a 40-fold without further optimization.
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