{"doi":"10.1021/jacs.5c09730","title":"Diversity-Oriented Method Development: Multifunctional Homoallylic Amines and Azabicyclooctanes Bearing a Bridgehead Enamine","abstract":"Two methods, designed primarily for applications in diversity-oriented synthesis (DOS), are introduced. The first is a Cu–H-catalyzed multicomponent process that involves a nitrile and a trisubstituted allenyl boronate. The first set of products are homoallylic α-secondary NH 2 -amines, containing a trisubstituted alkenyl boronate, formed with >98% enantiospecificity, in up to >98:2 dr and as a single alkene isomer (>98% Z ). The second method is efficient and diastereoselective triflic anhydride-mediated conversion of an unsaturated azapane-amide, generated from modification of the products of the foregoing catalytic process to azabicyclooctanes (ABCOs). The ABCOs contain a bridged enamine moiety and a trisubstituted alkene, which can be functionalized chemo- and stereoselectively. Accordingly, natural product-like rigid bicyclic frameworks can be obtained wherein four different fragments can be installed in space in a controllable fashion.","journal":"Journal of the American Chemical Society","year":2025,"id":524268,"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":4,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9504,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"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":1398333,"name":"Ryan P. Ponzi","orcid":null,"position":1,"is_corresponding":false},{"id":1032150,"name":"Xin Zhi Sui","orcid":"0000-0001-7435-2381","position":2,"is_corresponding":false},{"id":285942,"name":"Peng Liu","orcid":"0000-0002-8188-632X","position":3,"is_corresponding":false},{"id":308976,"name":"Amir H. Hoveyda","orcid":"0000-0002-1470-6456","position":4,"is_corresponding":false},{"id":1398332,"name":"Zoé C. Mueller","orcid":null,"position":0,"is_corresponding":true}],"reference_count":32,"raw_metadata":null,"created_at":"2026-07-19T02:50:12.083054Z","pmid":"40853977","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":[]}