ArticleAngewandte Chemie (International ed. in English)2022
Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters.
Article in Angewandte Chemie (International ed. in English), 2022. 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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9 citing papers in PubMed, 31 citations in OpenAlex.
- Eschenmoser's salts: from design to applications in organic synthesis.Organic chemistry frontiers : an international journal of organic chemistry · 2026Review
- Inductive Diastereoselective Rationale for a Catalytic Strategy to Build Densely Chiral Five-Membered Carbocycles.JACS Au · 2026Article
- 1,2-Migratory ring expansion of a BN-naphthalene.Organic & biomolecular chemistry · 2025Article
- Switchable Enantio- and Diastereoselective Michael Additions of β-Keto Amides to Nitroolefins: Crystallization-Based Inversion of Kinetic Stereocontrol.Organic letters · 2024Article
- Enantioselective Construction of Carbocyclic and Heterocyclic Tertiary Boronic Esters by Conjunctive Cross-Coupling Reaction.Journal of the American Chemical Society · 2023Article
- Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters.Angewandte Chemie (International ed. in English) · 2022Article
- Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement.Chemical science · 2022Article
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Authors and funding
3 authors at 1 institution in 1 country.
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Abstract
The synthesis of molecules bearing two or more contiguous, quaternary stereocenters is challenging, owing to the difficulty in controlling stereochemistry whilst simultaneously constructing a sterically congested motif. Herein, we report the electrophile-induced ring contractive 1,2-metallate rearrangement of 6-membered cyclic alkenyl boronate complexes for the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters with high levels of stereocontrol. Remarkably, simple variation of the reaction solvent enabled their diastereodivergent construction with facile access to complementary diastereomeric pairs. The utility of our methodology is demonstrated in the asymmetric total synthesis of (+)-herbertene-1,14-diol.
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