ArticleJournal of the American Chemical Society2017
Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Diastereoselective Synthesis of Axially Chiral Skipped Ene-Allenes Containing a Quaternary Stereocenter by Cyclopropene-Allene Metathesis.Angewandte Chemie (International ed. in English) · 2026Article
- Axially Chiral Spiro Compounds with Heavier Group 14 Elements as Spiro-Centers.Inorganic chemistry · 2026Article
- Lactam enables remote boronate rearrangements to C═N bonds.Communications chemistry · 2026Article
- Alkenyl- and Aryl-Borane Nucleophiles in Enantioselective Iridium-Catalyzed Allylic Substitution of Vinyl Epoxides.Journal of the American Chemical Society · 2025Article
- Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Stereoselective Synthesis of Axially Chiral Allenes and Styrenes via Chiral Phosphoric Acid Catalysis: An Overview.ACS omega · 2024Review
- Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis.Journal of the American Chemical Society · 2023Article
- Advances in the Asymmetric Synthesis of BINOL Derivatives.Molecules (Basel, Switzerland) · 2022Review
- Crown Ether-Derived Chiral BINOL: Enantioselective Michael Addition of Alkenyl Boronic Acids to α,β-Unsaturated Ketones.ACS omega · 2021Article
- Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones.Molecules (Basel, Switzerland) · 2021Article
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
- Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.Chemical reviews · 2021Article
- Reactivity and Synthetic Applications of Multicomponent Petasis Reactions.Chemical reviews · 2019Article
- Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.Journal of the American Chemical Society · 2019Article
- Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazinesRSC advances · 2019Article
- Article
- Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.Organic letters · 2019Article
- Article
- Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles.Chemical science · 2019Article
- Article
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4 authors.
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Abstract
Allenes are useful functional groups in synthesis as a result of their inherent chemical properties and established reactivity patterns. One property of chemical bonding renders 1,3-substituted allenes chiral, making them attractive targets for asymmetric synthesis. While there are many enantioselective methods to synthesize chiral allenes from chiral starting materials, fewer methods exist to directly synthesize enantioenriched chiral allenes from achiral precursors. We report here an asymmetric boronate addition to sulfonyl hydrazones catalyzed by chiral biphenols to access enantioenriched allenes in a traceless Petasis reaction. The resulting Mannich product from nucleophilic addition eliminates sulfinic acid, yielding a propargylic diazene that performs an alkyne walk to afford the allene. Two enantioselective approaches have been developed; alkynyl boronates add to glycolaldehyde imine to afford allylic hydroxyl allenes, and allyl boronates add to alkynyl imines to form 1,3-alkenyl allenes. In both cases, the products are obtained in high yields and enantioselectivities.
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