{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Cox L"],"funding":["Engineering and Physical Sciences Research Council"],"pagination":["e202206800"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9546487"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["61(34)"],"pubmed_abstract":["A Ti(Oi-Pr)<sub>4</sub> promoted 5- or 6-endo-trig cyclisation to make nitrogen heterocycles is presented. The utilisation of HFIP as a key solvent enables the stereoselective preparation of di- & tri-substituted pyrrolidines and piperidines while forming a new C-C bond at the same time. The process is triggered by a cationic intermediate generated from an allylic or benzylic alcohol and leads to the simultaneous generation of both a C-C and a C-N bond in a single step. Notably, either 2,3-trans- or 2,3-cis-substituted heterocycles can be obtained by using a nucleophilic amine bearing different substituents. Lastly, the stereoselective synthesis of enantiopure products was achieved by using readily available enantiopure acyclic starting materials."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Alcohols as Alkylating Agents in the Cation-Induced Formation of Nitrogen Heterocycles."],"pmcid":["PMC9546487"],"funding_grant_id":["EP/L015838/1"],"pubmed_authors":["Donohoe TJ","Sidera Portela M","Zhu Y","Christensen KE","Cox L","Smith PJ"],"additional_accession":[]},"is_claimable":false,"name":"Alcohols as Alkylating Agents in the Cation-Induced Formation of Nitrogen Heterocycles.","description":"A Ti(Oi-Pr)<sub>4</sub> promoted 5- or 6-endo-trig cyclisation to make nitrogen heterocycles is presented. The utilisation of HFIP as a key solvent enables the stereoselective preparation of di- & tri-substituted pyrrolidines and piperidines while forming a new C-C bond at the same time. The process is triggered by a cationic intermediate generated from an allylic or benzylic alcohol and leads to the simultaneous generation of both a C-C and a C-N bond in a single step. Notably, either 2,3-trans- or 2,3-cis-substituted heterocycles can be obtained by using a nucleophilic amine bearing different substituents. Lastly, the stereoselective synthesis of enantiopure products was achieved by using readily available enantiopure acyclic starting materials.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Aug","modification":"2025-04-04T20:04:40.05Z","creation":"2025-04-04T20:04:40.05Z"},"accession":"S-EPMC9546487","cross_references":{"pubmed":["35770710"],"doi":["10.1002/anie.202206800"]}}