{"doi":"10.1021/jo970186t","title":"Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels−Alder Reactions of <i>N</i>-Sulfinylphosphoramidates<sup>1</sup>","abstract":null,"journal":"The Journal of Organic Chemistry","year":1998,"id":676035,"datarank":0.8864573804198889,"base_score":2.639057329615259,"endowment":2.639057329615259,"self_citation_contribution":0.3958585994422889,"citation_network_contribution":0.49059878097759996,"self_endowment_contribution":0.3958585994422889,"citer_contribution":0.49059878097759996,"corpus_percentile":null,"corpus_rank":null,"citation_count":13,"citer_count":13,"citers_with_citation_signal":9,"citers_with_endowment":9,"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":1766422,"name":"Christopher J. Flann","orcid":null,"position":1,"is_corresponding":false},{"id":1766420,"name":"Yinsheng Zhang","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels−Alder Reactions of <i>N</i>-Sulfinylphosphoramidates<sup>1</sup>","abstract":"The [4 + 2] cycloaddition reactions of N -sulfinylphosphoramidates, prepared from the corresponding phosphoramidates by treatment with N -(chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (>95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.","is_dataset_classified":null,"base_score":2.639057329615259,"endowment":2.639057329615259,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"26207759","pmcid":null,"openalex_id":"https://openalex.org/W2084312134","authors":[],"funders":[],"total_grants":0,"fwci":1.3115,"citation_percentile":0.77207543,"influential_citations":0,"citation_trend":[{"year":2023,"count":1},{"year":2025,"count":1}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/jo970186t","host_type":"publisher"},{"url":"https://doi.org/10.1021/jo970186t","host_type":"journal"}],"fields_of_study":["Phosphorus compounds and reactions","Synthesis and Reactivity of Sulfur-Containing Compounds","Organophosphorus compounds synthesis"],"mesh_terms":[],"keywords":["Cycloaddition","Lewis acids and bases","Adduct","Chemistry","Reactivity (psychology)","Lewis acid catalysis","Catalysis","Medicinal chemistry","Yield (engineering)","Tin","Imidazole","Reaction mechanism","Stereochemistry","Organic chemistry","Materials science"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-17T01:59:53.809401Z","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":[]}