ArticleAngewandte Chemie (International ed. in English)2018
Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Successive Ring Expansion Strategies for the Synthesis of Macrocycles and Medium-Sized Rings.Chemical reviews · 2026Article
- Modular Assembly of Macrocyclic Sulfonamides via Consecutive Cascade Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions.Journal of the American Chemical Society · 2024Article
- Stereoselectivity control in Rh-catalyzed β-OH elimination for chiral allene formation.Nature communications · 2023Article
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
- Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from spNature communications · 2021Article
- Stereospecific 1,2-Migrations of Boronate Complexes Induced by Electrophiles.Angewandte Chemie (International ed. in English) · 2020Review
- Point-to-Axial Chirality Transmission: A Highly Sensitive Triaryl Chirality Probe for Stereochemical Assignments of Amines.The Journal of organic chemistry · 2020Article
- Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.Angewandte Chemie (International ed. in English) · 2018Article
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Authors and funding
6 authors.
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Abstract
An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched, point-chiral boronic esters were synthesized by homologation of α-seleno alkenyl boronic esters with lithiated carbamates and eliminated to form axially chiral allene products. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes.
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Registered trials
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