{"doi":"10.1021/jacs.2c02063","title":"Stereoselective 1,2-<i>cis</i> Furanosylations Catalyzed by Phenanthroline","abstract":"Stereoselective formation of the 1,2-cis furanosidic linkage, a motif of many biologically relevant oligosaccharides and polysaccharides, remains an important synthetic challenge. We herein report a new stereoselective 1,2-cis furanosylation method promoted by phenanthroline catalysts under mild and operationally simple conditions. NMR experiments and density functional theory calculations support an associative mechanism in which the rate-determining step occurs from an inverted displacement of the faster-reacting phenanthrolinium ion intermediate with an alcohol nucleophile. The phenanthroline catalysis system is applicable to a number of furanosyl bromide donors to provide the challenging 1,2-cis substitution products in good yield with high anomeric selectivities. While arabinofuranosyl bromide provides β-1,2-cis products, xylo- and ribofuranosyl bromides favor α-1,2-cis products.","journal":"Journal of the American Chemical Society","year":2022,"id":240918,"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":43,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9488,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2022-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":869058,"name":"Richard N. Schaugaard","orcid":"0000-0003-3351-8810","position":1,"is_corresponding":false},{"id":775269,"name":"Jiayi Li","orcid":"0000-0002-0179-1348","position":2,"is_corresponding":false},{"id":869059,"name":"H. Bernhard Schlegel","orcid":"0000-0001-7114-2821","position":3,"is_corresponding":false},{"id":458460,"name":"Hien M. Nguyen","orcid":"0000-0002-7626-8439","position":4,"is_corresponding":false},{"id":869505,"name":"Hengfu Xu","orcid":null,"position":0,"is_corresponding":true}],"reference_count":56,"raw_metadata":null,"created_at":"2026-07-19T00:22:51.435773Z","pmid":"35413194","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":[]}