{"doi":"10.1021/jacs.4c17174","title":"Ketenimines as Aza-Dienophiles","abstract":"High Resolution Image Download MS PowerPoint Slide N -Aryl ketenimines have been established as highly reactive aza-dienophiles. Intermolecular cycloadditions are achieved upon heating in the presence of 2,5-bis(silyloxy)furans and proceed with high levels of peri-, regio-, chemo- and diastereo-selectivity. Spontaneous C–O cleavage yields oxygenated pyridone derivatives in a highly convergent and redox-neutral manner. Combined experimental and computational studies demonstrate N -aryl ketenimines to be significantly more reactive than imino dienophiles, as a consequence of less distorted transition states. Derivatization studies include the development of isocyanate and cyclic ketenimine equivalents as aza-dienophiles, while extension to a one-pot aza-Diels–Alder/oxa-Diels–Alder sequence provides a three-component approach to complex fused pyridone/pyran systems.","journal":"Journal of the American Chemical Society","year":2025,"id":512364,"datarank":0.3958585994422889,"base_score":2.639057329615259,"endowment":2.639057329615259,"self_citation_contribution":0.3958585994422889,"citation_network_contribution":0.0,"self_endowment_contribution":0.3958585994422889,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":13,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9503,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1372516,"name":"G. Goyal","orcid":null,"position":1,"is_corresponding":false},{"id":1372517,"name":"Marshall J. Liss","orcid":null,"position":2,"is_corresponding":false},{"id":1372518,"name":"Jessica E. Budwitz","orcid":null,"position":3,"is_corresponding":false},{"id":1372519,"name":"Mary Stuart Herlihy","orcid":null,"position":4,"is_corresponding":false},{"id":1372520,"name":"Audrey V. Conner","orcid":null,"position":5,"is_corresponding":false},{"id":799231,"name":"Steven E. Wheeler","orcid":"0000-0001-7824-6906","position":6,"is_corresponding":false},{"id":1014029,"name":"Pengchen Ma","orcid":"0000-0002-4110-4696","position":7,"is_corresponding":false},{"id":604857,"name":"M Li","orcid":null,"position":8,"is_corresponding":false},{"id":292448,"name":"K. N. Houk","orcid":"0000-0002-8387-5261","position":9,"is_corresponding":false},{"id":1371851,"name":"Christopher G. Newton","orcid":"0000-0002-8962-5917","position":10,"is_corresponding":false},{"id":1372515,"name":"Christopher J. DeAngelis","orcid":null,"position":0,"is_corresponding":true}],"reference_count":59,"raw_metadata":{"citation_network_status":"fetched"},"created_at":"2026-07-19T02:48:06.263458Z","pmid":"39916527","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":[]}