ArticleJournal of the American Chemical Society2018
Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.Chemical science · 2026Article
- Pathway-divergent coupling of alkynes and cyclobutenes through enantioselective cobalt catalysis.Nature communications · 2025Article
- Can Twisted Double Bonds Facilitate Stepwise [2 + 2] Cycloadditions?Organic letters · 2024Article
- Tandem Isomerization/α,β-Site-Selective and Enantioselective Addition Reactions ofJournal of the American Chemical Society · 2023Article
- C(spChemical science · 2023Article
- Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.Accounts of chemical research · 2023Article
- Formal γ-C-H Functionalization of Cyclobutyl Ketones: Synthesis of cis-1,3-Difunctionalized Cyclobutanes.Angewandte Chemie (International ed. in English) · 2023Article
- Thermal and (Thermo-Reversible) Photochemical Cycloisomerization of 1Journal of the American Chemical Society · 2023Article
- Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids.Tetrahedron · 2022Article
- A New Paradigm in Enantioselective Cobalt Catalysis: Cationic Cobalt(I) Catalysts for Heterodimerization, Cycloaddition, and Hydrofunctionalization Reactions of Olefins.Accounts of chemical research · 2021Article
- Catalytic asymmetric synthesis of spirocyclobutyl oxindoles and beyondChemical science · 2021Article
- Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.Organic letters · 2020Article
- Chiral 1,3,2-Oxazaborolidine Catalysts for Enantioselective Photochemical Reactions.Accounts of chemical research · 2020Article
- Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes.Journal of the American Chemical Society · 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
- Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.Journal of the American Chemical Society · 2019Article
- Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.Journal of the American Chemical Society · 2019Article
- Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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3 authors.
Funding
Abstract
Identification of a novel catalyst-allenoate pair allows enantioselective [2+2] cycloaddition of α-methylstyrene. To understand the origin of selectivity, a detailed mechanistic investigation was conducted. Herein, two competing reaction pathways are proposed, which operate simultaneously and funnel the alkenes to the same axially chiral cyclobutanes. In agreement with the Woodward-Hoffmann rules, this mechanistic curiosity can be rationalized through a unique symmetry operation that was elucidated by deuteration experiments. In the case of 1,1-diarylalkenes, distal communication between the catalyst and alkene is achieved through subtle alteration of electronic properties and conformation. In this context, a Hammett study lends further credibility to a concerted mechanism. Thus, extended scope exploration, including β-substitution on the alkene to generate two adjacent stereocenters within the cyclobutane ring, is achieved in a highly stereospecific and enantioselective fashion (33 examples, up to >99:1 er).
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