{"doi":"10.1021/acs.joc.0c01132","title":"Utilization of the Thorpe–Ingold Effect in the Synthesis of Cyclooctanoid Ring Systems via Anionic 6-<i>exo</i>-<i>dig</i> Cyclization/Claisen Rearrangement Sequence","abstract":"We demonstrate a facile approach for the synthesis of gem-disubstituted cyclooctanoids, a motif found in several biologically active compounds. Appropriately substituted 1-alkenyl-5-pentyn-1-ols bearing gem-dialkyl substituents at either the C2, C3, or C4 position serve as useful precursors to a number of cyclooct-4-enone derivatives via a tandem, microwave-assisted oxyanionic 6-exo-dig cyclization/Claisen rearrangement reaction. gem-Dialkyl activation is necessary for these reactions to occur, as unactivated 1-alkenyl-5-pentyn-1-ols fail to undergo 6-exo-dig cyclization under the conditions employed. Further application of the methodology to the corresponding gem-dialkoxy system was also explored to facilitate access to more complex carbocycles.","journal":"The Journal of Organic Chemistry","year":2020,"id":71633,"datarank":0.8113226029776057,"base_score":2.8903717578961645,"endowment":2.8903717578961645,"self_citation_contribution":0.4335557636844247,"citation_network_contribution":0.37776683929318094,"self_endowment_contribution":0.4335557636844247,"citer_contribution":0.37776683929318094,"corpus_percentile":null,"corpus_rank":null,"citation_count":17,"citer_count":17,"citers_with_citation_signal":15,"citers_with_endowment":15,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9498,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":378490,"name":"Elizabeth A. Stone","orcid":"0000-0002-2253-3452","position":1,"is_corresponding":false},{"id":378491,"name":"Kimberly A. Alley","orcid":"0000-0003-3457-8495","position":2,"is_corresponding":false},{"id":379780,"name":"Victoria Iannarone","orcid":null,"position":3,"is_corresponding":false},{"id":379781,"name":"Emily M. Tarsis","orcid":null,"position":4,"is_corresponding":false},{"id":379782,"name":"Sami I. Ovaska","orcid":null,"position":5,"is_corresponding":false},{"id":378492,"name":"Timo V. Ovaska","orcid":"0000-0002-7540-9287","position":6,"is_corresponding":false},{"id":378489,"name":"Weston C. DeLomba","orcid":"0000-0002-3220-0475","position":0,"is_corresponding":true}],"reference_count":36,"raw_metadata":{"citation_network_status":"fetched"},"created_at":"2026-07-18T21:44:25.469842Z","pmid":"32687712","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}