{"doi":"10.3762/bjoc.20.255","title":"Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline <i>N</i> , <i>N’</i> -dioxide","abstract":"Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure-reactivity and selectivity relationship study. The observed catalyst structure-enantioselectivity relationship of the present allenylation reaction was found exactly opposite to that of the analogous allylation reaction. The method provided eleven α-allenic alcohols in 22-99% yield with 61:39-92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl-allenyl isomerization of propargyltrichlorosilane were computationally investigated.","journal":"Beilstein Journal of Organic Chemistry","year":2024,"id":482370,"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":0.9509,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1322582,"name":"Sreerag N. Moorkkannur","orcid":"0000-0001-5075-6947","position":1,"is_corresponding":false},{"id":875730,"name":"Anne Burns","orcid":null,"position":2,"is_corresponding":false},{"id":1322949,"name":"Layla Auter","orcid":null,"position":3,"is_corresponding":false},{"id":1322583,"name":"Valentino Cesiliano","orcid":"0009-0005-1076-3313","position":4,"is_corresponding":false},{"id":883548,"name":"Rajeev Prabhakar","orcid":"0000-0003-1137-1272","position":5,"is_corresponding":false},{"id":783450,"name":"Norito Takenaka","orcid":"0000-0003-3542-1086","position":6,"is_corresponding":false},{"id":1322948,"name":"Noble Brako","orcid":null,"position":0,"is_corresponding":true}],"reference_count":61,"raw_metadata":null,"created_at":"2026-07-19T02:07:14.349221Z","pmid":"39624656","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":[]}