{"doi":"10.24820/ark.5550190.p011.441","title":"Addition of heteroatom nucleophiles to ketene dimers","abstract":"An investigation of the reaction of heteroatom nucleophiles with ketene dimers, with an emphasis on a discussion of diastereoselectivity where applicable, is described. During this study we focused on the reaction of nitrogen-centred nucleophiles (Weinreb amine, lithiated Weinreb amide, and an amino acid derivative), and oxygen-centred nucleophiles (alkoxides). Simple Weinreb amide derivatives of ketene heterodimers were formed in moderate to excellent yield (up to 89%) and excellent retention of chirality (ee up to 91%), albeit with poor diastereoselectivity. The 2-pyridone-catalysed amine ring-opening was also applied to the asymmetric synthesis of a cinnabaramide A intermediate. Finally, the use of amide and alkoxide ring-opening nucleophiles enabled the development of a sequential one-pot reaction with benzaldehyde to afford -lactones in moderate yields (up to 47%) but with good diastereoselectivity (dr up to 24:1).","journal":"ARKIVOC","year":2021,"id":211754,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":1,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9558,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2021-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":801749,"name":"Gero D. Harzmann","orcid":null,"position":1,"is_corresponding":false},{"id":801750,"name":"Divya Nalla","orcid":null,"position":2,"is_corresponding":false},{"id":801751,"name":"Beth Elledge","orcid":null,"position":3,"is_corresponding":false},{"id":801752,"name":"Max Van Raaphorst","orcid":null,"position":4,"is_corresponding":false},{"id":436161,"name":"Nessan J. Kerrigan","orcid":"0000-0003-3643-5260","position":5,"is_corresponding":false},{"id":437018,"name":"Ahmad Ibrahim","orcid":null,"position":0,"is_corresponding":true}],"reference_count":34,"raw_metadata":null,"created_at":"2026-07-18T23:52:20.112538Z","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":[]}