{"doi":"10.1021/jacs.8b09297","title":"Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release","abstract":null,"journal":"Journal of the American Chemical Society","year":2018,"id":672056,"datarank":0.519860385419959,"base_score":3.4657359027997265,"endowment":3.4657359027997265,"self_citation_contribution":0.519860385419959,"citation_network_contribution":0.0,"self_endowment_contribution":0.519860385419959,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":31,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1755814,"name":"Takaaki Kobashi","orcid":null,"position":1,"is_corresponding":false},{"id":1755815,"name":"Kazuhiko Takai","orcid":"0000-0002-2572-0851","position":2,"is_corresponding":false},{"id":1755813,"name":"Sobi Asako","orcid":"0000-0003-4525-5317","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release","abstract":"Cyclopropanation of alkenes is a well-established textbook reaction for the synthesis of cyclopropanes, where a \"high-energy\" carbene species is exploited to drive the reaction forward. However, little attention has been focused toward molecular transformations involving the reverse reaction, retro-cyclopropanation (RC). This is because of difficulties associated with both cleaving the two geminal C-C single bonds and exploiting the generated carbenes for further transformations in an efficient and selective manner. Here, we report that a molybdenum-based catalytic system overcomes the above challenges and effects the RC of cyclopropanes bearing a pyridyl group with the release of ethylene (alkene) and the subsequent intramolecular cyclization leading to pyrido[2,1- a]isoindoles. The reaction allows for the uncommon use of cyclopropanes as C1 synthetic units in contrast to most conventional reactions in which cyclopropanes are used as C3 synthetic units. We anticipate that this new strategy will pave the way for C1 cyclopropane chemistry.","is_dataset_classified":null,"base_score":3.4657359027997265,"endowment":3.4657359027997265,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"30347153","pmcid":null,"openalex_id":"https://openalex.org/W2898019013","authors":[],"funders":[{"funder_name":"Ministry of Education, Culture, Sports, Science and Technology","grant_id":"17K19122","title":null},{"funder_name":"Ministry of Education, Culture, Sports, Science and Technology","grant_id":"26248030","title":null}],"total_grants":2,"fwci":1.7784,"citation_percentile":0.84065065,"influential_citations":0,"citation_trend":[{"year":2019,"count":8},{"year":2020,"count":2},{"year":2021,"count":7},{"year":2022,"count":7},{"year":2023,"count":2},{"year":2024,"count":1},{"year":2025,"count":3},{"year":2026,"count":1}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://doi.org/10.1021/jacs.8b09297.s001","host_type":"BRONZE"},{"url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.8b09297","host_type":"publisher"},{"url":"https://doi.org/10.1021/jacs.8b09297","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/30347153","host_type":"repository"}],"fields_of_study":["Cyclopropane Reaction Mechanisms","Catalytic Alkyne Reactions","Synthetic Organic Chemistry Methods","Medicine","Chemistry"],"mesh_terms":[],"keywords":["Cyclopropanation","Cyclopropane","Chemistry","Alkene","Intramolecular force","Geminal","Carbene","Ethylene","Catalysis","Combinatorial chemistry","Stereochemistry","Organic chemistry","Ring (chemistry)"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Affordable and clean energy"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-16T06:11:27.875880Z","pmid":null,"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":[]}