{"doi":"10.1021/acs.joc.1c01466","title":"Sequential Norrish–Yang Cyclization and C–C Cleavage/Cross-Coupling of a [4.1.0] Fused Saturated Azacycle","abstract":"Methods that functionalize the periphery of azacylic scaffolds have garnered increasing interest in recent years. Herein, we investigate the selectivity of a solid-state Norrish-Yang cyclization (NYC) and subsequent C-C cleavage/cross-coupling reaction of a strained cyclopropane-fused azacyclic system. Surprisingly, the NYC primarily furnished a single lactam constitutional and diastereo-isomer. The regioselectivity of the C-C cleavage of the α-hydroxy-β-lactam moiety could be varied by altering the ligand set used in the coupling chemistry. Experimental and computational observations are discussed.","journal":"The Journal of Organic Chemistry","year":2021,"id":182211,"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":15,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9555,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2021-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":344079,"name":"Bohyun Park","orcid":"0000-0003-0552-8763","position":1,"is_corresponding":false},{"id":308340,"name":"Liping Xu","orcid":"0000-0001-6421-062X","position":2,"is_corresponding":false},{"id":308337,"name":"Jose B. Roque","orcid":"0000-0002-5449-1584","position":3,"is_corresponding":false},{"id":308346,"name":"Charles S. Yeung","orcid":"0000-0001-7320-7190","position":4,"is_corresponding":false},{"id":305804,"name":"Djamaladdin G. Musaev","orcid":"0000-0003-1160-6131","position":5,"is_corresponding":false},{"id":308347,"name":"Richmond Sarpong","orcid":"0000-0002-0028-6323","position":6,"is_corresponding":false},{"id":734042,"name":"Rebecca Lyn LaLonde","orcid":"0000-0001-7062-0166","position":7,"is_corresponding":false},{"id":308343,"name":"Charis Amber","orcid":"0000-0002-3671-5388","position":0,"is_corresponding":true}],"reference_count":20,"raw_metadata":null,"created_at":"2026-07-18T23:48:09.223560Z","pmid":"34399579","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":[]}