{"doi":"10.1002/adsc.200505162","title":"Synthesis of New <i>C</i><sub>2</sub>‐Symmetrical Bissulfonamide Ligands and Application in the Enantioselective Addition of Alkynylzinc to Aldehydes and Ketones","abstract":"<jats:title>Abstract</jats:title><jats:p>Novel <jats:italic>C</jats:italic><jats:sub>2</jats:sub>‐symmetrical bissulfonamide ligands were easily prepared in three simple steps and applied in the enantioselective addition of alkynylzinc reagents to aldehydes. Compound <jats:bold>7a</jats:bold> was found to be an outstanding ligand for this reaction. When the catalyst loading, 4 mol % of <jats:bold>7a</jats:bold>, was used, high enantioselectivity with an ee value up to 97% was achieved under very mild conditions. When the amount of ligand <jats:bold>7a</jats:bold> was lowered to 2 mol %, excellent levels of enantiocontrol up to 95% ee were still achieved. So far the most economic catalyst system was developed for the addition of terminal alkynes to aromatic aldehydes in terms of ligand loading and enantioselectivity. Moreover, ligand <jats:bold>7a</jats:bold> in combination with Ti(O‐<jats:italic>i</jats:italic>‐Pr)<jats:sub>4</jats:sub> was found to be effective in promoting the addition reaction of an alkynylzinc reagent to unactivated simple ketones under very mild conditions. The corresponding chiral tertiary propargylic alcohols were obtained with enantiomeric excesses of up to 81%.</jats:p>","journal":"Advanced Synthesis &amp; Catalysis","year":2005,"id":658993,"datarank":0.5676284450877392,"base_score":3.784189633918261,"endowment":3.784189633918261,"self_citation_contribution":0.5676284450877392,"citation_network_contribution":0.0,"self_endowment_contribution":0.5676284450877392,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":43,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":816285,"name":"Rui Wang","orcid":"0000-0001-8007-2503","position":1,"is_corresponding":false},{"id":1720310,"name":"Zhi‐jian Han","orcid":null,"position":2,"is_corresponding":false},{"id":401933,"name":"Bin Mao","orcid":"0000-0002-3792-3787","position":3,"is_corresponding":false},{"id":1720311,"name":"Chao‐shan Da","orcid":null,"position":4,"is_corresponding":false},{"id":1078768,"name":"Lei Liu","orcid":"0000-0003-3943-6381","position":5,"is_corresponding":false},{"id":1006790,"name":"Chao Chen","orcid":"0000-0002-7939-6241","position":6,"is_corresponding":false},{"id":78336,"name":"Ming Ni","orcid":"0000-0001-9465-2787","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Synthesis of New <i>C</i><sub>2</sub>‐Symmetrical Bissulfonamide Ligands and Application in the Enantioselective Addition of Alkynylzinc to Aldehydes and Ketones","abstract":"<jats:title>Abstract</jats:title><jats:p>Novel <jats:italic>C</jats:italic><jats:sub>2</jats:sub>‐symmetrical bissulfonamide ligands were easily prepared in three simple steps and applied in the enantioselective addition of alkynylzinc reagents to aldehydes. Compound <jats:bold>7a</jats:bold> was found to be an outstanding ligand for this reaction. When the catalyst loading, 4 mol % of <jats:bold>7a</jats:bold>, was used, high enantioselectivity with an ee value up to 97% was achieved under very mild conditions. When the amount of ligand <jats:bold>7a</jats:bold> was lowered to 2 mol %, excellent levels of enantiocontrol up to 95% ee were still achieved. So far the most economic catalyst system was developed for the addition of terminal alkynes to aromatic aldehydes in terms of ligand loading and enantioselectivity. Moreover, ligand <jats:bold>7a</jats:bold> in combination with Ti(O‐<jats:italic>i</jats:italic>‐Pr)<jats:sub>4</jats:sub> was found to be effective in promoting the addition reaction of an alkynylzinc reagent to unactivated simple ketones under very mild conditions. The corresponding chiral tertiary propargylic alcohols were obtained with enantiomeric excesses of up to 81%.</jats:p>","is_dataset_classified":null,"base_score":3.784189633918261,"endowment":3.784189633918261,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"19162232","pmcid":null,"openalex_id":"https://openalex.org/W2082917983","authors":[],"funders":[],"total_grants":0,"fwci":3.4312,"citation_percentile":0.92676461,"influential_citations":0,"citation_trend":[{"year":2012,"count":3},{"year":2013,"count":1},{"year":2014,"count":4},{"year":2015,"count":3},{"year":2016,"count":1},{"year":2025,"count":1},{"year":2026,"count":2}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200505162","host_type":"publisher"},{"url":"https://advanced.onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200505162","host_type":"publisher"},{"url":"https://doi.org/10.1002/adsc.200505162","host_type":"journal"},{"url":"http://ir.lzu.edu.cn/handle/262010/115736","host_type":"repository"}],"fields_of_study":["Synthetic Organic Chemistry Methods","Asymmetric Synthesis and Catalysis","Sulfur-Based Synthesis Techniques"],"mesh_terms":[],"keywords":["Enantioselective synthesis","Chemistry","Reagent","Ligand (biochemistry)","Catalysis","Enantiomer","Enantiomeric excess","Reaction conditions","Combinatorial chemistry","Chiral ligand","Organic chemistry","Medicinal chemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-12T05:56:30.448168Z","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":[]}