{"doi":"10.1021/jacs.5c15956","title":"Enantioselective Trifunctionalization of Terminal Alkynes","abstract":"The stereoselective synthesis of alkenes has been one of the central objectives in organic chemistry. Significant advances in synthetic methodology have made mono- and disubstituted alkenes widely accessible from a variety of readily available precursors. However, increased steric hindrance in more highly substituted alkenes limits the effectiveness of these methods, and as a result, the efficient and selective synthesis of highly substituted alkenes remains a formidable challenge. Here, we demonstrate palladium-catalyzed trifunctionalization of terminal alkynes using organoboranes and allylic carbonates as coupling partners. This transformation provides tetrasubstituted alkenes with excellent regioselectivity and diastereoselectivity. Moreover, regiodivergent, diastereo- and enantioselective incorporation of the allylic fragment provides access to a wide range of complex 1,4-diene products. We present evidence that the palladium catalyst controls the selectivity of tetrasubstituted alkene formation and the selectivity of allylic substitution.","journal":"Journal of the American Chemical Society","year":2025,"id":515333,"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":6,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.95,"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":1380155,"name":"M. Cole Detels","orcid":null,"position":1,"is_corresponding":false},{"id":741833,"name":"Gojko Lalić","orcid":"0000-0003-3615-3423","position":2,"is_corresponding":false},{"id":1380154,"name":"Langxuan Yang","orcid":null,"position":0,"is_corresponding":true}],"reference_count":88,"raw_metadata":null,"created_at":"2026-07-19T02:48:39.436300Z","pmid":"41284687","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":[]}