ArticleAngewandte Chemie (International ed. in English)2018
Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.
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 16 papers.
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Who cites it
16 citing papers in PubMed.
- Phosphine-Catalyzed Unsymmetric [2 + 2] Annulation of Allenyl Phosphonates for Highly Substituted Cyclobutenes.Angewandte Chemie (International ed. in English) · 2026Article
- Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes.Nature communications · 2025Article
- Recent advances in the application of [2 + 2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products.Natural products and bioprospecting · 2024Review
- Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.Accounts of chemical research · 2023Article
- Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.Molecules (Basel, Switzerland) · 2023Review
- Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids.Tetrahedron · 2022Article
- Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.Letters in organic chemistry · 2022Article
- Access to substituted cyclobutenes by tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of dipropargylphosphonates under Ag/Co relay catalysis.Chemical science · 2020Article
- Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.Organic letters · 2020Article
- Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light.Organic letters · 2020Article
- Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.Journal of the American Chemical Society · 2020Article
- Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.Angewandte Chemie (International ed. in English) · 2020Article
- Recent advances in the synthesis of gem-dimethylcyclobutane natural products.Natural product reports · 2019Review
- Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.Journal of the American Chemical Society · 2019Article
- Thioallenoates in Catalytic Enantioselective [2+2]-Cycloadditions with Unactivated Alkenes.Tetrahedron · 2019Article
- Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.Journal of the American Chemical Society · 2018Article
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Abstract
The first synthesis of hebelophyllene E is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophyllene E. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and allenoates provides access to the required chiral geminal dimethylcyclobutanes. Key to its success is the identification of a novel oxazaborolidine catalyst which promotes the cycloaddition in high enantioselectivities with good functional-group tolerance (9 examples, up to 97:3 e.r.). Thus, a late-stage cycloaddition using a fully functionalized alkene, followed by a diastereoselective reduction allows a concise entry to this class of natural products.
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