ArticleAngewandte Chemie (International ed. in English)2020
Stereoselective Csp
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Total Synthesis of Voratin C: Formation of the [6,5]-Spiroketal Core through Acid-Mediated Epoxide Cascade Opening.Organic letters · 2026Article
- Stereospecific cross-coupling reactions: Programmed assembly of chiral molecules by reaction of chiral reagents.Science advances · 2025Review
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- Calculation-assisted regioselective functionalization of the imidazo[1,2-Chemical science · 2023Article
- Stereospecific Transformations of Alkylboronic Esters Enabled by Direct Boron-to-Zinc Transmetalation.Journal of the American Chemical Society · 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
- General stereoretentive preparation of chiral secondary mixed alkylmagnesium reagents and their use for enantioselective electrophilic aminations.Chemical science · 2021Article
- Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.Journal of the American Chemical Society · 2021Article
- Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands.Angewandte Chemie (International ed. in English) · 2021Article
- Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes.Chemical science · 2020Article
- Stereoselective CspAngewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report palladium-catalyzed cross-coupling reactions of chiral secondary non-stabilized dialkylzinc reagents, prepared from readily available chiral secondary alkyl iodides, with alkenyl and aryl halides. This method provides α-chiral alkenes and arenes with very high retention of configuration (dr up to 98:2) and satisfactory overall yields (up to 76 % for 3 reaction steps). The configurational stability of these chiral non-stabilized dialkylzinc reagents was determined and exceeded several hours at 25 °C. DFT calculations were performed to rationalize the stereoretention during the catalytic cycle. Furthermore, the cross-coupling reaction was applied in an efficient total synthesis of the sesquiterpenes (S)- and (R)-curcumene with control of the absolute stereochemistry.
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